General Organic Chemistry-03- Assignments

STUDY  INNOVATIONS
STUDY INNOVATIONSEducator en Study Innovations

SECTION - I SUBJECTIVE QUESTIONS LEVEL - I 1. Give the IUPAC name for the amine. CH3 | CH3 — N —C — CH2CH3 | | 2. Write the aci-form of nitromethane. CH3 C2H5 3. Draw Newman projections for the anti and gauche conformations of indicated stability of the conformers. (a) 1-bromo-2-chloroethane (b) 3-hydroxypropanoic acid 4. Classify the following as nucleophiles and electrophiles : (i) H3O+ (ii) NH3 (iii) AlCl3 (iv) ROH (iv) BF3 (v) CN– (vi) SO3 (vii) R—O—R 5. Arrange given compounds in order of decreasing acidity : (a) CH3 – NO2 (b) NO2 – CH2 – NO2 (c) CH3 – CH2 – NO2 (d) NO2  CH  NO2 | NO2 6. Give IUPAC names of the following compounds : (a) (b) CH  C  CH  CH  CHO || | | O OH Cl HOOC  CH2  CH  CH2  COOH | CH3 7. Arrange the following in decreasing order of their stability :     (a) CH3  C C6 H5 CH2 CH3 CH2 CH3  CH 3 2 I II III IV 8. How many isomers are possible for C3H6O. 9. C – C single bond length in propene appears to be less than C – C single bond length in propane. Why ? 10. How many Aromatic isomers are possible for CH2CH3 LEVEL - II 1. Explain why alkyl groups act as electron donors when attached to a p-system. 2. Convert the following formula for alanine to a Fischer projection : NH2 C H3C H3C COOH 3. Draw all possible stereoisomers of 2, 3-dichlorobutane. Indicate enantiomeric and diastereomeric pairs. 4. Do the following structures represent identical molecules or a pair of enantiomers? CH3 (a) C HO H OH and C C H CH3 C2H5 CH2Br 2 5 H H (b) C H and C OH HO CH3 CH3 CH2Br 5. Acid amides are amphoteric in nature. Explain. 6. Addition of HBr to 1-bromopropene on the presence of benzoyl peroxide gives 1-bromopropane as the main product. Justify. 7. Arrange basicity of the given compounds in decreasing order : (a) CH3 – CH2 – NH2 (b) CH2 = CH – NH2 (c) CH  C – NH2 8. Decreasing order of stability of given carbocations is as : (a) (b)  CH  CH  CH (c)  C H  CH  C H (d)  CH  CH  CH 6 5 6 5 3 3 9. Identify the pairs of enantiomers and diastereomers amongst the following compounds CH3 CH3 CH3 H (a) OH CH3 H OH CH3 (b) H CH3 OH H OH (c) 10. How many optical isomers are possible for H H H H LEVEL - III 1. Arrange the following in increasing order of acidic strength COOH OCH3 COOH OCH3 COOH OCH3 COOH 2. How many optically active isomers are possible for glucose and fructose. 3. Arrange the carbocations in increasing order of stability when the following compounds are treated with aqueous KOH. CH2Cl CH2Cl OCH3 CH2Cl CH3 CH2Cl NO2 4. Arrange the following in increasing order of melting point. CH3COOH HCOOH CH3CH2COOH CH3CH2CH2COOH 5. How many aromatic isomers are possible for C7H8O and total isomers for C4H6 6. An optically pure compound X gain an [] 25 = + 29.0°. A mixture of X and its enantiomer Y gain [] 25 = 10.0°. What is the ratio of X and Y

Chemistry : General Organic Chemistry & Isomerism
ASSIGNMENTS
SECTION - I
SUBJECTIVE QUESTIONS
LEVEL - I
1. Give the IUPAC name for the amine.
3
3 2 3
5
2
3
CH
|
CH —N —C —CH CH
|
|
C H
CH
2. Write the aci-form of nitromethane.
3. Draw Newman projections for theanti and gauche conformations of indicated stability of theconformers.
(a) 1-bromo-2-chloroethane (b) 3-hydroxypropanoic acid
4. Classify the following as nucleophiles and electrophiles :
(i) H3O+ (ii) NH3 (iii) AlCl3 (iv) ROH
(iv) BF3 (v) CN– (vi) SO3 (vii) R—O—R
5. Arrange given compounds in order of decreasing acidity :
(a) CH3
– NO2
(b) NO2
– CH2
– NO2
(c) CH3
– CH2
– NO2
(d) 2 2
2
NO CH NO
|
NO
 
6. Give IUPAC names of the following compounds :
(a) 3
CH C CH CH CHO
|| | |
O OH Cl
   
(b) 2 2
3
HOOC CH CH CH COOH
|
CH
   
7. Arrange the following in decreasing order of their stability :
(a)    
3 6 5 2 3 2 3
3 2
I II III IV
CH C C H CH CH CH CH CH
   
8. How many isomers are possible for C3
H6
O.
9. C – C single bond length in propene appears to be less than C – C single bond length in propane. Why ?
10. How many Aromatic isomers are possible for CH2
CH3
Chemistry : General Organic Chemistry & Isomerism
LEVEL - II
1. Explain why alkyl groups act as electron donors when attached to a p-system.
2. Convert the following formula for alanine to a Fischer projection :
C
NH2
COOH
C
H3
C
H3
3. Draw all possible stereoisomers of 2, 3-dichlorobutane. Indicate enantiomeric and diastereomeric pairs.
4. Do the following structures represent identical molecules or a pair of enantiomers?
(a) C
CH3
H
C2H5
O
H
and C
OH
CH3
H
C2H5
(b) C
CH2Br
OH
CH3
H
and C
H
CH3
CH2Br
O
H
5. Acid amides are amphoteric in nature. Explain.
6. Addition of HBr to 1-bromopropene on the presence of benzoyl peroxide gives 1-bromopropane as the
main product. Justify.
7. Arrange basicity of the given compounds in decreasing order :
(a) CH3
– CH2
– NH2
(b) CH2
= CH – NH2
(c) CH  C – NH2
8. Decreasing order of stability of given carbocations is as :
(a)
+
(b) 2 2
CH CH CH

 
(c) 6 5 6 5
C H CH C H

  (d) 3 3
CH CH CH

 
9. Identify the pairs of enantiomers and diastereomers amongst the following compounds
H OH
CH3
CH3
H
(a)
H
H
OH
OH
CH3 CH3
(b) (c)
H
CH3 OH
H
CH3
Chemistry : General Organic Chemistry & Isomerism
10. How many optical isomers are possible for
CH3
H H
H
H
H H
CH3
LEVEL - III
1. Arrange the following in increasing order of acidic strength
COOH
OCH3
COOH
OCH3
COOH
OCH3
COOH
2. How many optically active isomers are possible for glucose and fructose.
3. Arrange the carbocations in increasing order of stability when the following compounds are treated
with aqueous KOH.
CH2Cl CH2Cl
OCH3
CH2Cl
CH3
CH2Cl
NO2
4. Arrange the following in increasing order of melting point.
CH3
COOH HCOOH CH3
CH2
COOH CH3
CH2
CH2
COOH
5. How many aromatic isomers are possible for C7
H8
O and total isomers for C4
H6
6. An optically pure compound X gain an []0
25
= + 29.0°. A mixture of X and its enantiomer Y gain
[]0
25
= 10.0°. What is the ratio of X and Y in the mixutre.
7. Why amines are more basic than amide and cyanides.
8. Arrange the following compounds in increasing order of stability.
N N
H
N
H
O
N
H
9. The configuration of the chiral centre of the given compound
H OH
CH3
Br H
Et
is 2s, 3s explain.
Chemistry : General Organic Chemistry & Isomerism
10. Pick out the compound which can be obtained is an optically active from.
HOOC
HOOC
NO2
NO2
H
C
H3 H
COOH
H OH
COOH
O
H H
H OH
COOH
, ,
O2N
HOOC
NO2
COOH
.
Chemistry : General Organic Chemistry & Isomerism
SECTION - II
SINGLE CHOICE QUESTIONS
1. Consider the following carbanions :
(1) 3 2
CH CH

 (2) 2
CH CH


(3) CH C


Correct order of stability of these carbanions in decreasing order is
(a) 1 > 2 > 3 (b) 2 > 1 > 3
(c) 3 > 2 > 1 (d) 3 > 1 > 2
2. Consider the following carbocations :
(a) 2
CH CH

 (b) 3 2
CH CH


(c) 2 2
CH CH CH

  (d) 2
6 5
C H CH


Stability of these carbocations in decreasing order is
(a) 4 > 3 > 2 > 1 (b) 4 > 3 > 2 > 1
(c) 3 > 4 > 2 > 1 (d) 3 > 4 > 1 > 2
3. Which of the following compounds is most basic :
(a)
NH2
(b)
NH2
NO2
(c)
NH2
CN
(d)
NH2
CH3
4. Consider the following compounds :
(1)
N
H
(2)
N
(3)
N N
O
H
(4)
N
O
H
(4)
H
N
Order of basicity of these compounds in decreasing order is :
(a) 4 > 1 > 2 > 3 (b) 1 > 3 > 4 > 2
(c) 2 > 3 > 4 > 1 (d) 1 > 3 > 2 > 4
5. In which compound carbon-carbon bond length is maximum ?
(a) Ethane (b) Propene
(c) 2-butene (d) 2, 3-dimethyl-2-butene
Chemistry : General Organic Chemistry & Isomerism
6. Which of these species are electrophiles :
(a) CCl2
(b) BF3
(c) 2
NO

(d) All of these
7. Which of the following species is electrophile :
(a) OH

(b) 3
CH O


(c) BF3
(d) NH3
8. Acyl cation has two resonating structures (I) and (II)
   
I II
R C O R C O
 
    
Which statement is correct for (I) and (II)
(a) (I) is more stable than (II)
(b) (II) is more stable than (I)
(c) Stability of (I) and (II) will be the same
(d) For some time (I) will be more stable and for remaining time (II) will be more stable
9. Tautomerism is shown by
(a) 3 2 3
O O
| | | |
CH C CH C CH
    (b) 3 2 2 5
O O
| | | |
CH C CH COOC H
  
(c) 3 2
CH CH N
 
O
O
(d) All of these
10. Which one of the following compounds has maximum enol content in solution
(a) 3 2 2 5
O
||
CH C CH COOC H
   (b) 3 2
O
||
CH C CH CN
  
(c) 3 3
O
||
CH C CH
  (d) O
11. Which one of the following has the highest nucleophilicity
(a) F–
(b) OH–
(c) CH 3

(d) –
NH2
12. The most stable free radical is :
(a) 3 2
CH CH
 (b) 2 2
CH CH CH
 
(c) 3 3
CH CH CH
  (d) 3
CH
13. +R effect will be shown by :
(a) NO2
(b) —CN
(c) CHO (d) – NHCOCH3
Chemistry : General Organic Chemistry & Isomerism
14. The number of delocalised  -electrons in the given compound is

(a) 4 (b) 6
(c) 8 (d) 2
15. In pyridine :
N
:
Number of conjugated electrons are ;
(a) 6 (b) 8
(c) Zero (d) 5
16. Consider the following isomeric alkanes
(1) n-pentane (2) Isopentane
(3) Neopentane
Arrange bp of these compounds in decreasing order :
(a) 1 > 2 > 3 (b) 3 > 2 > 1
(c) 1 > 3 > 2 (d) 3 > 1 > 2
17. In which of the following structures the pair of carbon atoms do not lie in the same plane
(a)
H C
3
C == C
CH3
H
CH _ H C
3 2
*
*
(b)
CH3
*
*
(c)
CH ==C
*
*
H
H (d)
H C
3
C == C
H
CH _ CH
2 3
*
*
H C
3
18. In which of the following molecules all the effects namely inductive, mesomeric and hyperconjugation
operate
(a) (b) 3
COCH
3
CH
(c)
3
CH
3
CH (d)
19. Most acidic hydrogen is present in
(a)
O O
(b)
O
(c) (CH3
CO)3
CH (d) None of these
20. Which one of the following chlorides gives white precipitate with AgNO3
most readily
(a) CH3
= CH – CH2
Cl (b) CH2
= CH– Cl
(c) CH3
– CH2
– CH2
Cl (d) (C6
H5
)2
CH – Cl
Chemistry : General Organic Chemistry & Isomerism
SECTION - III
MULTIPLE CHOICE QUESTIONS
1. Carbanion (X) loses a leaving group to form alkene which is/are correct statements?
CH3
CH3
C
H3
C
H3
H L
H , I


CH3
CH3
C
H3
C
H3
L
L
II




CH3
C
H3
CH3
C
H3
(a) It is E2
type (b) It is E1
type
(c) It is E1-CB type (d) Step I is fast and II is slow
2. In which case/cases SE
will be in meta position?
(a) N2
(b) NH C
O
CH3
(c) N(CH3)3 (d) CF3
3. Which of the following cannot undergo nucleophilic substitution under ordinary condition?
(a) Benzyl chloride (b) Allyl chloride
(c) Vinyl chloride (d) n-Propyl chloride
4. HCN and HNC are which type of isomers?
(a) Position (b) Chain
(c) Tautomers (d) Functional
5. Which is/are correct statements for
A B
(a) A is Z and B is E (b) A and B are same structures
(c) A is cis and B is trans (d) A is R and B is S
6. Which of the following is an optically active compound?
(a) 1, 3-Butadiene (b) Propadiene
(c) 2, 3-Pentadiene (d) 1, 3-Pentadiene
7. Which of the following will show geometrical isomerism?
(a) HO—N==N—OH (b) CH3
CH2
NO2
(c) (d) C NOH
C
H3
C
H3
Chemistry : General Organic Chemistry & Isomerism
8. Which of the following pairs of compounds are tautomers?
(a) Propanal and propanone (b) 1-Propanol and 2-Propanol
(c) Ethanol and vinyl alcohol (d) Vinyl alcohol and ethanal
9. Geometric isomerism will be exhibited by
(a) 1-Pentene (b) 3-Methyl-1-butene
(c) 2-Pentene (d) All of these compounds
10. Which of the following compounds is not chiral?
(a) DCH2
CD2
CH2
Cl (b) 3 2
CH CH CH—Cl
|
D
(c) CH3
CHDCH2
Cl (d) CH3
CHCl·CH2
D
Chemistry : General Organic Chemistry & Isomerism
MISCELLANEOUS QUESTIONS
SECTION - IV
COMPREHENSION TYPE QUESTIONS
Write up - I
Isomers which are nonsuper-imposable mirror images of each other are called enantiomers. All optically
active compounds exhibit enantiomerims. The stereoisomers which are not mirror images of each
other are called diastereomers. Enantiomers are always chiral molecules wheres diastereomers may
or may not be chiral, configuration of the compound having no element of symmetry is always chiral.
Chiral molecule may or may not contain chiral carbon.
1. Which of the following compounds are chiral?
(a)
2
CHO
|
H —C — OH
|
CH OH
(b)
C C
H
C
H3
C
C2H5
H
(c)
Br
Cl
C
CH3
H
(d) all of these
2. Which of the following pairs are diastereomers?
(a)
3 3
CHO CHO
| |
H —C —OH and HO —C — H
| |
CH CH
(b)
H C
COOH
C
Br
Br H
C6H5
Br C
COOH
C
H
H Br
C6H5
and
(c) C C
H
CH3
C
H3
H
C C
CH3
H
C
H3
H
and (d) all of these
3. Which statement is correct for enantiomers :
(a) Both are non-superimposable mirror images
(b) Both are superimposable mirror images
(c) Physical properties are different
(d) Reaction velocity with optically active compound is same
Chemistry : General Organic Chemistry & Isomerism
Write up - II
Delocalisation of electrons take place in alternate single and multiple bonds involving carbon atoms.
Delocalisation may also occur in a conjugated system involving carbon atom and atom other than the
carbon. There are also examples in which pi orbital and p orbital (vacant or half-filled or filled)
overlap. Thus delocalisation are of the following types :
(i) delocalisation by ,  overlap
(ii) delocalisation by , p overlap
Delocalisation makes system stable. More is the number of resonating structures more is the stability
of the system.
4. In which of the following compounds delocalisation is not possible
(a) 1, 4-pentadiene (b) 1, 3-butadiene
(c) 1, 3, 5-hexatriene (d) benzene
5. Arrange the following resonating structures of formic acid in decreasing order of stability.
(I)
O
||
H —C —O — H (II)
O
|
H —C O— H



(III)
O
|
H —C—OH


(IV)
O
|
H —C—OH


(a) I > II > IV > III (b) I > II > III > IV
(c) IV > III > II > I (d) I > IV > II > III
6. Which one of the following carbocation is most stable due to the resonance?
(a) (b) 6 5 2
C H — CH

(c) 6 5 6 5
C H — CH — C H

(d) 6 5 6 5
3
C H —C —C H
|
CH

Chemistry : General Organic Chemistry & Isomerism
MULTIPLE MATCHING TYPE QUESTIONS
Match the following
7. Column A Column B
(A) CH2
=CH2
+ HBr in presence of oxygen (1) Carbocation
(B) Dehydrobromination of
2-methyl-2-bromopropane (2) Carbanion
(C) Alkaline hydrolysis of chloroform (3) Free radical
(D) Rearrangement not possible in (4) Carbene
(A) (B) (C) (D)
(a) 1, 3 2 3, 4 2
(b) 2, 3 1, 3 4 3
(c) 1, 4 3 2 1
(d) 3 1 4 2, 3, 4
8. Column A Column B
(A) sp (1) Carbocation
(B) sp2
(2) Carbanion
(C) sp3
(3) Free radical
(D) Both sp2
and sp3
(4) Triplet carbene
(A) (B) (C) (D)
(a) 2 2 3, 4 1
(b) 2 2, 3, 4 2 1
(c) 3 2, 3, 4 1 2
(d) 4 3 2 1
9. Column A Column B
(A) C6
H5
CH2
CD2
Br on reacting with
C2
H5
O–
gives C6
H5
—CH==CD2
(1) E1
(B) PhCHBrCH3
and PhCHBrCD3
both
react with the same rate. (2) E2
(C) C6
H5
CH2
CH2
Br on treatment
with C2
H5
O–
and C2
H5
OD
gives C6
H5
CD==CH2
(3) E1CB
(D) C6
H5
CH2
CH2
Br reacts faster
than C6
H5
CD2
CH2
Br on reaction
with C2
H5
O–
in ethanol (4) First order reaction
Chemistry : General Organic Chemistry & Isomerism
(A) (B) (C) (D)
(a) 1, 4 2 3 2, 3
(b) 2 1, 4 3 2
(c) 2 1, 4 1, 3 2, 3
(d) 1, 4, 2, 3 3 2
ASSERTION-REASON TYPE QUESTIONS
The question given below consist of an ASSERTION and the REASON. Use the following key for the
appropriate answers
(a) If both Assertion and Reason are correct and Reason is the correct explanation for Assertion
(b) If both Assertion and Reason are correct and Reason is not the correct explanation for
Assertion
(c) If Assertion is correct but Reason is not correct.
(d) If Assertion is incorrect but Reason is correct.
10. Assertion : Cyclobutane is more reactive than cyclopentane.
Reason : The carbocyclic ring in cyclobutane is more strained than in cyclopentane.
11. Assertion : SN
1 reaction of 2-chloro-3, 3-dimethylbutane with NaOH gives 2, 3-dimethyl-2-butanol as
the major product.
Reason : Intermediate is a secondary carbocation which undergoes 1, 2-methyl shift giving more
stable tertiary carbocation.
12. Assertion : Hyperconjugation results in thestabilisationo f carbocation by delocalising the positive charge.
Reason : Hyperconjugation produces some additional bonding between the electron-deficient carbon
and the adjacent carbon.
13. Assertion : Ortho-hydroxy benzoic acid is much more acidic than benzoic acid.
Reason : Anion formed from ortho-hydroxy benzoic acid is stabilised by hydrogen bonding.
14. Assertion : The carbocation CF3
—C+
H2
is less stable than C+
F3
.
Reason : In case of CF3
—C+H
2, CF3 is strong electron withdrawing therefore increases +ve charge
when in C+F3, Ione pair of F overlap with vacant p-orbital of carbon reducing +ve change by
p-pt bonding or back bonding.
15. Assertion : The Friedel craft alkylation of nitrobenzene gives meta alkylated nitrobenzene.
Reason : Nitrogroups an meta directing.
Chemistry : General Organic Chemistry & Isomerism
SECTION - V
(PROBLEMS )
A. Only one option is correct (Objective Questions)
1. Among the following, the least stable resonance structure is
(a) N
O
O
(b) N
O
O
(c) N
O
O
(d) N
O
O
2. The IUPAC name of C6
H5
COCl is :
(a) Benzoyl chloride (b) Benzene chloro ketone
(c) Benzene carbonyl chloride (d) Chloro phenyl ketone
3. 4-methyl benzene sulphonic acid reacts with sodium acetate to give :
(a)
CH3
SO3Na
; CHCOOH (b)
COONa
CH3
; SO3
(c)
CH3
; SO3
(d)
O2S
CH3
OCOCH3
; NaOH
4. Which of the following resonating structures of 1-methyoxy-1, 3-butadiene is least stable?
(a) 2 3
CH — CH CH — CH O— CH
 
 
(b) 2 2 3
CH CH — CH — CH O— CH
 
 
(c) 2 3
CH — CH — CH CH — O — CH
 

(d) 2 3
CH CH — CH — CH — O — CH
 

Chemistry : General Organic Chemistry & Isomerism
5. Arrange in order of increasing acidic strength
N
+
H3
H3N
+
COOH
Z
X
Y
(a) X > Z > Y (b) Z < X > Y
(c) X > Y > Z (d) Z > X > Y
6. C2
is rotated anticlockwise 120°C about C2
—C3
bond. The resulting conformer is :
CH3
H
H
H
CH3
H
3
2
(a) partially eclipsed (b) eclipsed
(c) gauche (d) staggered
7. Among the following the molecule with the highest dipole moment is :
(a) CH3
Cl (b) CH2
Cl2
(c) CHCl3
(d) CCl4
8. Which of the following represent the given mode of hybridization sp2
– sp2
– sp – sp from left to right?
(a) H2
C==CH—CCH (b) HCC—C—CCH
(c) H2
C==C==C==CH2
(d) C
H2
CH2
9. Which of the following hydrocarbons has the lowest dipole moment?
(a) C C
H
CH3
C
H3
H
(b) CH3
—HC==HC—CH3
(c) CH3
—CH2
CH==CH2
(d) CH2
==CH—CH==CH2
10. Which of the following compounds exhibits, stereoisomerism?
(a) 2-methyl butene-1 (b) 3-methyl butyne-1
(c) 3-methyl butanoic acid (d) 2-methyl butanoic acid
Chemistry : General Organic Chemistry & Isomerism
B. More than one options are correct (Objective Questions)
1. Only two isomeric monochloro derivatives are possible for :
(a) n-butane (b) 2, 4-dimethyl pentane
(c) benzene (d) 2-methyl propane
2. The compound in which C uses its sp3
- hybrid orbitals for bond formation is :
(a) HCOOH (b) (H2
N)2
CO
(c) (CH3
)3
COH (d) CH3
CHO
3. Which of the following have asymmetric carbon atom?
(a) H C C H
H
Cl
H
Br
(b) H C C Cl
H
H
H
Cl
(c) H C C D
H
H
H
Cl
(d) H C C CH3
Br
H
OH
H
4. The molecules that will have dipole moment are :
(a) 2, 2 dimethyl propane (b) trans 2-pentene
(c) cis-3-hexene (d) 2, 2, 3, 3-tetramethyl butane
5. What is the decreasing order of strength of the bases :
2 3 2
OH , NH , H — C C and CH — CH ?
   

(a) 3 2 2
CH — CH NH H — C C OH
   
   
(b) 3 2 2
H — C C CH — CH NH OH
   
   
(c) 2 3 2
OH NH H — C C CH — CH
   
   
(d) 2 3 2
NH H — C C OH CH — CH
   
   
6. Which of the following compounds will show geometrical isomerism?
(a) 2-butene (b) propene
(c) 1-phenyl propane (d) 2-methyl butene
7. Tautomerism is exhibited by :
(a) CH==CH—OH (b) O O
(c) O
O
(d) O
O
Chemistry : General Organic Chemistry & Isomerism
C. Assertion-Reason Type Questions
1. In the following a statement (S) in the left hand column and an explanation (E) in the right hand column.
Ascertain the relationship between S and E and select the correct code among a, b, c and d which are
defined below :
(a) Both S and E are true, and E is the correct explanation of S
(b) Both S and E are true, but E is not the correct explanation of S
(c) S is true but E is false
(d) S is false but E is true
Statement (S) : p-Hydroxybenzoic acid has a lower boiling point than o-hydroxybenzoic acid.
Explanation (E) :o-Hydroxybenzoic acid has intramolecular hydrogen bonding.
SUBJECTIVEQUESTIONS
1. Write the IUPAC name of CH3CH2CH==CH·COOH
2. Give the IUPAC name of the following compound :
Me
Me
Me
Me
Me
(Me = methyl)
3. Write the IUPAC name for the following :
C
H3 N C CH2 CH3
CH3 C2H5
CH3
4. Write tautomeric forms of phenol.
5. Draw the setreochemical structures of the products in the following reactions :
(i) Br H
C2H5
C2H5
2
N
NaOH
S


(ii) 2
H
Lindlar catalyst
R — C C — R
 
6. Write down the structures of the stereoisomers formed when cis-2-butene is reacted with bromine.
7. Discuss the hybridization of carbon atoms in alkene (C3H4) and show the -orbital overlaps.
Chemistry : General Organic Chemistry & Isomerism
8. Identify the pairs of enantiomers and diastereomers from the following :
H OH
CH3
O
H H
CH3
I
O
H H
CH3
O
H H
CH3
II
O
H H
CH3
H OH
CH3
III
9. (a) Draw Newmann’s projection for the less stable staggered form of butane.
(b) Relatively less stability of the staggered form is due to :
(i) Torsional strain
(ii) van der Waal’s strain
(iii) Combination of the above two
10. obs ix
   l
where l is the dipole moment of stable conformer and xi is the mole fraction of that conformer.
.
(a) Write stable conformer for Z—CH2—CH2—Z in Newmann’s projection.
If µsolution = 1.0 D and mole fraction of anti form = 0.82, find µGauche
(b) Write most stable meso conformer of
CHDY
|
CHDY
If (i) Y = CH3 about C2—C3 rotation and
(ii) Y = OH about C! —C2 rotation.
Chemistry : General Organic Chemistry & Isomerism
ANSWERS
EXERCISE - 1
1. (3 Cyano Propanal) 2. (3 Ethyl 2, 5 di Methyl hexane)
3. (2, 3 dipoxy pentane) 4. (3 Chloro Pentanidoi Acid)
EXERCISE - 2
1. (4) 2. (4)
3. (2) 4. (3)
5. (2)
EXERCISE - 3
1. (3) 2. (2)
3. (1) 4. (4)
5. (3) 6. (2)
EXERCISE - 4
1. (a) C6H5
+
is a vinyl carbocation and is less stable than C6H11
+
, a 2° carbocation.
(b) In C6
H5
: –
, the electron pair is in an sp2
hybrid orbital. The carbanion has more s-character and is
more stable than C6
H11
: –
whose unshared electron pair is in an sp3
hybrid orbital.
EXERCISE - 5
1. (a) There are four stereoisomers. A and B are enantiomers, are are C and D.
(b) A and B are diastereomers of C and D.
CH3
C H5
2
Cl
H
HO H
CH3
C H5
2
H
Cl
H OH
(A) (B)
(racemate)1
CH3
C H5
2
Cl
H
H HO
CH3
C H5
2
H
Cl
HO H
(C) (D)
(racemate)2
2. Cyclopentane is best considered as a flat ring. All trans-isomers exist as a pair of enantiomers. All cis-
isomers are meso.
Chemistry : General Organic Chemistry & Isomerism
Me
Me
Me
Me
racemate
trans–1, 2-Dimethylcyclopentane
Me
Me
meso
cis –1, 2-Dimethylcyclopentane
Me
Me Me
Me
racemate
trans–1, 3-Dimethylcyclopentane
meso
cis –1, 3-Dimethylcyclopentane
Me Me
+
C H
6 5
+
+
C H
6 11
+
H –
C H
6 5:
–
sp
2
C H
6 11:
–
H
–
sp
3
SECTION - I
(Subjective Questions)
Answers are given in the separate booklet (Level – I to Level – III)
SECTION - II
(Single Choice Questions)
1. (c) 2. (a)
3. (d) 4. (d)
5. (a) 6. (d)
7. (c) 8. (b)
9. (d) 10. (d)
11. (c) 12. (b)
13. (d) 14. (b)
15. (a) 16. (a)
17. (d) 18. (b)
19. (c) 20. (d)
Chemistry : General Organic Chemistry & Isomerism
SECTION - III
(Multiple Choice Questions)
1. (c, d) 2. (c, d)
3. (d) 4. (c, d)
5. (a, c) 6. (c)
7. (a, b, c) 8. (d)
9. (c) 10. (a)
SECTION - IV
(Comprehension Type Questions)
1. (d) 2. (c)
3. (a) 4. (a)
5. (b) 6. (d)
(Multiple Matching Type Questions)
7. (d) 8. (b)
9. (b)
(Assertion Reason Type Questions)
10. (b)
11. (a) 12. (a)
13. (a) 14. (a)
15. (d)
SECTION - V
A. Only one option is correct (Objective Questions)
1. (a) 2. (c)
Chemistry : General Organic Chemistry & Isomerism
3. (a) 4. (c)
5. (a) 6. (c)
7. (a) 8. (a)
9. (b) 10. (d)
C. Assertion-reason type questions
1. (d)
SUBJECTIVE
Answers are given in the separate booklet.

Recomendados

WORK BOOK_P_IV.doc por
WORK BOOK_P_IV.docWORK BOOK_P_IV.doc
WORK BOOK_P_IV.docSTUDY INNOVATIONS
8 vistas19 diapositivas
Acidicity basicity & H- Bonding Tautomerism (Q.B.)13th.pdf por
Acidicity basicity & H- Bonding Tautomerism (Q.B.)13th.pdfAcidicity basicity & H- Bonding Tautomerism (Q.B.)13th.pdf
Acidicity basicity & H- Bonding Tautomerism (Q.B.)13th.pdfSTUDY INNOVATIONS
12 vistas16 diapositivas
General Organic Chemistry-02-Solved Problems por
 General Organic Chemistry-02-Solved Problems General Organic Chemistry-02-Solved Problems
General Organic Chemistry-02-Solved ProblemsSTUDY INNOVATIONS
9 vistas10 diapositivas
DPP-9- PC por
DPP-9- PCDPP-9- PC
DPP-9- PCSTUDY INNOVATIONS
5 vistas2 diapositivas
WORK BOOK_P_VIII.doc por
WORK BOOK_P_VIII.docWORK BOOK_P_VIII.doc
WORK BOOK_P_VIII.docSTUDY INNOVATIONS
9 vistas16 diapositivas
Alcohols Ethers and Pheno-03- Assignments por
Alcohols Ethers and Pheno-03- Assignments Alcohols Ethers and Pheno-03- Assignments
Alcohols Ethers and Pheno-03- Assignments STUDY INNOVATIONS
28 vistas26 diapositivas

Más contenido relacionado

Similar a General Organic Chemistry-03- Assignments

Basic principles in organic chemistry --exercise with solutions por
Basic principles in organic chemistry --exercise with solutionsBasic principles in organic chemistry --exercise with solutions
Basic principles in organic chemistry --exercise with solutionssuresh gdvm
11.3K vistas34 diapositivas
DPP-44 to 45- PC por
DPP-44 to 45- PCDPP-44 to 45- PC
DPP-44 to 45- PCSTUDY INNOVATIONS
6 vistas4 diapositivas
Hydrocarbon-05- Assignments por
Hydrocarbon-05- AssignmentsHydrocarbon-05- Assignments
Hydrocarbon-05- AssignmentsSTUDY INNOVATIONS
11 vistas20 diapositivas
Electrophilic Aromatic Substitution-03-Assignments por
Electrophilic Aromatic Substitution-03-Assignments Electrophilic Aromatic Substitution-03-Assignments
Electrophilic Aromatic Substitution-03-Assignments STUDY INNOVATIONS
19 vistas18 diapositivas
Resonance (Q.B.)12th.pdf por
Resonance (Q.B.)12th.pdfResonance (Q.B.)12th.pdf
Resonance (Q.B.)12th.pdfSTUDY INNOVATIONS
4 vistas11 diapositivas
Class 12 Cbse Chemistry Sample Paper 2010 Model-3 por
Class 12 Cbse Chemistry Sample Paper 2010 Model-3Class 12 Cbse Chemistry Sample Paper 2010 Model-3
Class 12 Cbse Chemistry Sample Paper 2010 Model-3Sunaina Rawat
702 vistas17 diapositivas

Similar a General Organic Chemistry-03- Assignments(20)

Basic principles in organic chemistry --exercise with solutions por suresh gdvm
Basic principles in organic chemistry --exercise with solutionsBasic principles in organic chemistry --exercise with solutions
Basic principles in organic chemistry --exercise with solutions
suresh gdvm11.3K vistas
Electrophilic Aromatic Substitution-03-Assignments por STUDY INNOVATIONS
Electrophilic Aromatic Substitution-03-Assignments Electrophilic Aromatic Substitution-03-Assignments
Electrophilic Aromatic Substitution-03-Assignments
STUDY INNOVATIONS19 vistas
Class 12 Cbse Chemistry Sample Paper 2010 Model-3 por Sunaina Rawat
Class 12 Cbse Chemistry Sample Paper 2010 Model-3Class 12 Cbse Chemistry Sample Paper 2010 Model-3
Class 12 Cbse Chemistry Sample Paper 2010 Model-3
Sunaina Rawat702 vistas
CAPE Chemistry Unit 2 Paper 1 2010 por Zara_Mohammed
CAPE Chemistry Unit 2 Paper 1 2010CAPE Chemistry Unit 2 Paper 1 2010
CAPE Chemistry Unit 2 Paper 1 2010
Zara_Mohammed4.2K vistas
Orgainic Chemistry-05-SUBJECTIVE PROBLEMS (BASIC LEVEL) por STUDY INNOVATIONS
Orgainic Chemistry-05-SUBJECTIVE PROBLEMS (BASIC LEVEL)Orgainic Chemistry-05-SUBJECTIVE PROBLEMS (BASIC LEVEL)
Orgainic Chemistry-05-SUBJECTIVE PROBLEMS (BASIC LEVEL)
Organicchemistrydiscretestestw 140928163032-phpapp02 por Cleophas Rwema
Organicchemistrydiscretestestw 140928163032-phpapp02Organicchemistrydiscretestestw 140928163032-phpapp02
Organicchemistrydiscretestestw 140928163032-phpapp02
Cleophas Rwema190 vistas
10116-part-3-inorg.pdf por moumitaroy58
10116-part-3-inorg.pdf10116-part-3-inorg.pdf
10116-part-3-inorg.pdf
moumitaroy5883 vistas

Más de STUDY INNOVATIONS

Science-Class-12 Physics and Chemistry DPP Talent Search Examinations por
Science-Class-12 Physics and Chemistry DPP Talent Search ExaminationsScience-Class-12 Physics and Chemistry DPP Talent Search Examinations
Science-Class-12 Physics and Chemistry DPP Talent Search ExaminationsSTUDY INNOVATIONS
5 vistas15 diapositivas
Science-Class-12 Maths DPP Talent Search Examinations por
Science-Class-12 Maths DPP Talent Search ExaminationsScience-Class-12 Maths DPP Talent Search Examinations
Science-Class-12 Maths DPP Talent Search ExaminationsSTUDY INNOVATIONS
6 vistas3 diapositivas
Science-Class-11 Physics and Chemistry DPP Talent Search Examinations por
Science-Class-11 Physics and Chemistry DPP Talent Search ExaminationsScience-Class-11 Physics and Chemistry DPP Talent Search Examinations
Science-Class-11 Physics and Chemistry DPP Talent Search ExaminationsSTUDY INNOVATIONS
11 vistas14 diapositivas
Science-Class-11 Maths DPP Talent Search Examinations por
Science-Class-11 Maths DPP Talent Search ExaminationsScience-Class-11 Maths DPP Talent Search Examinations
Science-Class-11 Maths DPP Talent Search ExaminationsSTUDY INNOVATIONS
5 vistas3 diapositivas
Science-Class-11 Biology DPP Talent Search Examinations por
Science-Class-11 Biology DPP Talent Search ExaminationsScience-Class-11 Biology DPP Talent Search Examinations
Science-Class-11 Biology DPP Talent Search ExaminationsSTUDY INNOVATIONS
6 vistas9 diapositivas
Science-Class-10 DPP Talent Search Examinations por
Science-Class-10 DPP Talent Search ExaminationsScience-Class-10 DPP Talent Search Examinations
Science-Class-10 DPP Talent Search ExaminationsSTUDY INNOVATIONS
8 vistas12 diapositivas

Más de STUDY INNOVATIONS(20)

Science-Class-12 Physics and Chemistry DPP Talent Search Examinations por STUDY INNOVATIONS
Science-Class-12 Physics and Chemistry DPP Talent Search ExaminationsScience-Class-12 Physics and Chemistry DPP Talent Search Examinations
Science-Class-12 Physics and Chemistry DPP Talent Search Examinations
Science-Class-12 Maths DPP Talent Search Examinations por STUDY INNOVATIONS
Science-Class-12 Maths DPP Talent Search ExaminationsScience-Class-12 Maths DPP Talent Search Examinations
Science-Class-12 Maths DPP Talent Search Examinations
Science-Class-11 Physics and Chemistry DPP Talent Search Examinations por STUDY INNOVATIONS
Science-Class-11 Physics and Chemistry DPP Talent Search ExaminationsScience-Class-11 Physics and Chemistry DPP Talent Search Examinations
Science-Class-11 Physics and Chemistry DPP Talent Search Examinations
STUDY INNOVATIONS11 vistas
Science-Class-11 Maths DPP Talent Search Examinations por STUDY INNOVATIONS
Science-Class-11 Maths DPP Talent Search ExaminationsScience-Class-11 Maths DPP Talent Search Examinations
Science-Class-11 Maths DPP Talent Search Examinations
Science-Class-11 Biology DPP Talent Search Examinations por STUDY INNOVATIONS
Science-Class-11 Biology DPP Talent Search ExaminationsScience-Class-11 Biology DPP Talent Search Examinations
Science-Class-11 Biology DPP Talent Search Examinations
Science-Class-10 DPP Talent Search Examinations por STUDY INNOVATIONS
Science-Class-10 DPP Talent Search ExaminationsScience-Class-10 DPP Talent Search Examinations
Science-Class-10 DPP Talent Search Examinations
Science-Class-9 DPP Talent Search Examinations por STUDY INNOVATIONS
Science-Class-9 DPP Talent Search ExaminationsScience-Class-9 DPP Talent Search Examinations
Science-Class-9 DPP Talent Search Examinations
STUDY INNOVATIONS11 vistas
Science-Class-8 DPP Talent Search Examinations por STUDY INNOVATIONS
Science-Class-8 DPP Talent Search ExaminationsScience-Class-8 DPP Talent Search Examinations
Science-Class-8 DPP Talent Search Examinations
Mathematics-Class-10 DPP Talent Search Examinations por STUDY INNOVATIONS
Mathematics-Class-10 DPP Talent Search ExaminationsMathematics-Class-10 DPP Talent Search Examinations
Mathematics-Class-10 DPP Talent Search Examinations
Mathematics-Class-8 DPP Talent Search Examinations por STUDY INNOVATIONS
Mathematics-Class-8 DPP Talent Search ExaminationsMathematics-Class-8 DPP Talent Search Examinations
Mathematics-Class-8 DPP Talent Search Examinations
Mathematics-Class-7 DPP Talent Search Examinations por STUDY INNOVATIONS
Mathematics-Class-7 DPP Talent Search ExaminationsMathematics-Class-7 DPP Talent Search Examinations
Mathematics-Class-7 DPP Talent Search Examinations
Mathematics-Class-6 DPP Talent Search Examinations por STUDY INNOVATIONS
Mathematics-Class-6 DPP Talent Search ExaminationsMathematics-Class-6 DPP Talent Search Examinations
Mathematics-Class-6 DPP Talent Search Examinations
Mathematics-Class-4 DPP Talent Search Examinations por STUDY INNOVATIONS
Mathematics-Class-4 DPP Talent Search ExaminationsMathematics-Class-4 DPP Talent Search Examinations
Mathematics-Class-4 DPP Talent Search Examinations
STUDY INNOVATIONS11 vistas
Mathematics-Class-3 DPP Talent Search Examinations por STUDY INNOVATIONS
Mathematics-Class-3 DPP Talent Search ExaminationsMathematics-Class-3 DPP Talent Search Examinations
Mathematics-Class-3 DPP Talent Search Examinations
Mathematics-Class-2 DPP Talent Search Examinations por STUDY INNOVATIONS
Mathematics-Class-2 DPP Talent Search ExaminationsMathematics-Class-2 DPP Talent Search Examinations
Mathematics-Class-2 DPP Talent Search Examinations
Mathematics-Class-1 DPP Talent Search Examinations por STUDY INNOVATIONS
Mathematics-Class-1 DPP Talent Search ExaminationsMathematics-Class-1 DPP Talent Search Examinations
Mathematics-Class-1 DPP Talent Search Examinations

Último

The Open Access Community Framework (OACF) 2023 (1).pptx por
The Open Access Community Framework (OACF) 2023 (1).pptxThe Open Access Community Framework (OACF) 2023 (1).pptx
The Open Access Community Framework (OACF) 2023 (1).pptxJisc
85 vistas7 diapositivas
231112 (WR) v1 ChatGPT OEB 2023.pdf por
231112 (WR) v1  ChatGPT OEB 2023.pdf231112 (WR) v1  ChatGPT OEB 2023.pdf
231112 (WR) v1 ChatGPT OEB 2023.pdfWilfredRubens.com
144 vistas21 diapositivas
EIT-Digital_Spohrer_AI_Intro 20231128 v1.pptx por
EIT-Digital_Spohrer_AI_Intro 20231128 v1.pptxEIT-Digital_Spohrer_AI_Intro 20231128 v1.pptx
EIT-Digital_Spohrer_AI_Intro 20231128 v1.pptxISSIP
317 vistas50 diapositivas
CWP_23995_2013_17_11_2023_FINAL_ORDER.pdf por
CWP_23995_2013_17_11_2023_FINAL_ORDER.pdfCWP_23995_2013_17_11_2023_FINAL_ORDER.pdf
CWP_23995_2013_17_11_2023_FINAL_ORDER.pdfSukhwinderSingh895865
507 vistas6 diapositivas
The Accursed House by Émile Gaboriau por
The Accursed House  by Émile GaboriauThe Accursed House  by Émile Gaboriau
The Accursed House by Émile GaboriauDivyaSheta
158 vistas15 diapositivas
Gopal Chakraborty Memorial Quiz 2.0 Prelims.pptx por
Gopal Chakraborty Memorial Quiz 2.0 Prelims.pptxGopal Chakraborty Memorial Quiz 2.0 Prelims.pptx
Gopal Chakraborty Memorial Quiz 2.0 Prelims.pptxDebapriya Chakraborty
598 vistas81 diapositivas

Último(20)

The Open Access Community Framework (OACF) 2023 (1).pptx por Jisc
The Open Access Community Framework (OACF) 2023 (1).pptxThe Open Access Community Framework (OACF) 2023 (1).pptx
The Open Access Community Framework (OACF) 2023 (1).pptx
Jisc85 vistas
EIT-Digital_Spohrer_AI_Intro 20231128 v1.pptx por ISSIP
EIT-Digital_Spohrer_AI_Intro 20231128 v1.pptxEIT-Digital_Spohrer_AI_Intro 20231128 v1.pptx
EIT-Digital_Spohrer_AI_Intro 20231128 v1.pptx
ISSIP317 vistas
The Accursed House by Émile Gaboriau por DivyaSheta
The Accursed House  by Émile GaboriauThe Accursed House  by Émile Gaboriau
The Accursed House by Émile Gaboriau
DivyaSheta158 vistas
Plastic waste.pdf por alqaseedae
Plastic waste.pdfPlastic waste.pdf
Plastic waste.pdf
alqaseedae125 vistas
Use of Probiotics in Aquaculture.pptx por AKSHAY MANDAL
Use of Probiotics in Aquaculture.pptxUse of Probiotics in Aquaculture.pptx
Use of Probiotics in Aquaculture.pptx
AKSHAY MANDAL89 vistas
Compare the flora and fauna of Kerala and Chhattisgarh ( Charttabulation) por AnshulDewangan3
 Compare the flora and fauna of Kerala and Chhattisgarh ( Charttabulation) Compare the flora and fauna of Kerala and Chhattisgarh ( Charttabulation)
Compare the flora and fauna of Kerala and Chhattisgarh ( Charttabulation)
AnshulDewangan3316 vistas
JiscOAWeek_LAIR_slides_October2023.pptx por Jisc
JiscOAWeek_LAIR_slides_October2023.pptxJiscOAWeek_LAIR_slides_October2023.pptx
JiscOAWeek_LAIR_slides_October2023.pptx
Jisc79 vistas
Drama KS5 Breakdown por WestHatch
Drama KS5 BreakdownDrama KS5 Breakdown
Drama KS5 Breakdown
WestHatch71 vistas
Structure and Functions of Cell.pdf por Nithya Murugan
Structure and Functions of Cell.pdfStructure and Functions of Cell.pdf
Structure and Functions of Cell.pdf
Nithya Murugan368 vistas
Narration ppt.pptx por TARIQ KHAN
Narration  ppt.pptxNarration  ppt.pptx
Narration ppt.pptx
TARIQ KHAN119 vistas
ISO/IEC 27001 and ISO/IEC 27005: Managing AI Risks Effectively por PECB
ISO/IEC 27001 and ISO/IEC 27005: Managing AI Risks EffectivelyISO/IEC 27001 and ISO/IEC 27005: Managing AI Risks Effectively
ISO/IEC 27001 and ISO/IEC 27005: Managing AI Risks Effectively
PECB 545 vistas
AI Tools for Business and Startups por Svetlin Nakov
AI Tools for Business and StartupsAI Tools for Business and Startups
AI Tools for Business and Startups
Svetlin Nakov101 vistas
Psychology KS4 por WestHatch
Psychology KS4Psychology KS4
Psychology KS4
WestHatch68 vistas
Community-led Open Access Publishing webinar.pptx por Jisc
Community-led Open Access Publishing webinar.pptxCommunity-led Open Access Publishing webinar.pptx
Community-led Open Access Publishing webinar.pptx
Jisc74 vistas
Ch. 7 Political Participation and Elections.pptx por Rommel Regala
Ch. 7 Political Participation and Elections.pptxCh. 7 Political Participation and Elections.pptx
Ch. 7 Political Participation and Elections.pptx
Rommel Regala72 vistas

General Organic Chemistry-03- Assignments

  • 1. Chemistry : General Organic Chemistry & Isomerism ASSIGNMENTS SECTION - I SUBJECTIVE QUESTIONS LEVEL - I 1. Give the IUPAC name for the amine. 3 3 2 3 5 2 3 CH | CH —N —C —CH CH | | C H CH 2. Write the aci-form of nitromethane. 3. Draw Newman projections for theanti and gauche conformations of indicated stability of theconformers. (a) 1-bromo-2-chloroethane (b) 3-hydroxypropanoic acid 4. Classify the following as nucleophiles and electrophiles : (i) H3O+ (ii) NH3 (iii) AlCl3 (iv) ROH (iv) BF3 (v) CN– (vi) SO3 (vii) R—O—R 5. Arrange given compounds in order of decreasing acidity : (a) CH3 – NO2 (b) NO2 – CH2 – NO2 (c) CH3 – CH2 – NO2 (d) 2 2 2 NO CH NO | NO   6. Give IUPAC names of the following compounds : (a) 3 CH C CH CH CHO || | | O OH Cl     (b) 2 2 3 HOOC CH CH CH COOH | CH     7. Arrange the following in decreasing order of their stability : (a)     3 6 5 2 3 2 3 3 2 I II III IV CH C C H CH CH CH CH CH     8. How many isomers are possible for C3 H6 O. 9. C – C single bond length in propene appears to be less than C – C single bond length in propane. Why ? 10. How many Aromatic isomers are possible for CH2 CH3
  • 2. Chemistry : General Organic Chemistry & Isomerism LEVEL - II 1. Explain why alkyl groups act as electron donors when attached to a p-system. 2. Convert the following formula for alanine to a Fischer projection : C NH2 COOH C H3 C H3 3. Draw all possible stereoisomers of 2, 3-dichlorobutane. Indicate enantiomeric and diastereomeric pairs. 4. Do the following structures represent identical molecules or a pair of enantiomers? (a) C CH3 H C2H5 O H and C OH CH3 H C2H5 (b) C CH2Br OH CH3 H and C H CH3 CH2Br O H 5. Acid amides are amphoteric in nature. Explain. 6. Addition of HBr to 1-bromopropene on the presence of benzoyl peroxide gives 1-bromopropane as the main product. Justify. 7. Arrange basicity of the given compounds in decreasing order : (a) CH3 – CH2 – NH2 (b) CH2 = CH – NH2 (c) CH  C – NH2 8. Decreasing order of stability of given carbocations is as : (a) + (b) 2 2 CH CH CH    (c) 6 5 6 5 C H CH C H    (d) 3 3 CH CH CH    9. Identify the pairs of enantiomers and diastereomers amongst the following compounds H OH CH3 CH3 H (a) H H OH OH CH3 CH3 (b) (c) H CH3 OH H CH3
  • 3. Chemistry : General Organic Chemistry & Isomerism 10. How many optical isomers are possible for CH3 H H H H H H CH3 LEVEL - III 1. Arrange the following in increasing order of acidic strength COOH OCH3 COOH OCH3 COOH OCH3 COOH 2. How many optically active isomers are possible for glucose and fructose. 3. Arrange the carbocations in increasing order of stability when the following compounds are treated with aqueous KOH. CH2Cl CH2Cl OCH3 CH2Cl CH3 CH2Cl NO2 4. Arrange the following in increasing order of melting point. CH3 COOH HCOOH CH3 CH2 COOH CH3 CH2 CH2 COOH 5. How many aromatic isomers are possible for C7 H8 O and total isomers for C4 H6 6. An optically pure compound X gain an []0 25 = + 29.0°. A mixture of X and its enantiomer Y gain []0 25 = 10.0°. What is the ratio of X and Y in the mixutre. 7. Why amines are more basic than amide and cyanides. 8. Arrange the following compounds in increasing order of stability. N N H N H O N H 9. The configuration of the chiral centre of the given compound H OH CH3 Br H Et is 2s, 3s explain.
  • 4. Chemistry : General Organic Chemistry & Isomerism 10. Pick out the compound which can be obtained is an optically active from. HOOC HOOC NO2 NO2 H C H3 H COOH H OH COOH O H H H OH COOH , , O2N HOOC NO2 COOH .
  • 5. Chemistry : General Organic Chemistry & Isomerism SECTION - II SINGLE CHOICE QUESTIONS 1. Consider the following carbanions : (1) 3 2 CH CH   (2) 2 CH CH   (3) CH C   Correct order of stability of these carbanions in decreasing order is (a) 1 > 2 > 3 (b) 2 > 1 > 3 (c) 3 > 2 > 1 (d) 3 > 1 > 2 2. Consider the following carbocations : (a) 2 CH CH   (b) 3 2 CH CH   (c) 2 2 CH CH CH    (d) 2 6 5 C H CH   Stability of these carbocations in decreasing order is (a) 4 > 3 > 2 > 1 (b) 4 > 3 > 2 > 1 (c) 3 > 4 > 2 > 1 (d) 3 > 4 > 1 > 2 3. Which of the following compounds is most basic : (a) NH2 (b) NH2 NO2 (c) NH2 CN (d) NH2 CH3 4. Consider the following compounds : (1) N H (2) N (3) N N O H (4) N O H (4) H N Order of basicity of these compounds in decreasing order is : (a) 4 > 1 > 2 > 3 (b) 1 > 3 > 4 > 2 (c) 2 > 3 > 4 > 1 (d) 1 > 3 > 2 > 4 5. In which compound carbon-carbon bond length is maximum ? (a) Ethane (b) Propene (c) 2-butene (d) 2, 3-dimethyl-2-butene
  • 6. Chemistry : General Organic Chemistry & Isomerism 6. Which of these species are electrophiles : (a) CCl2 (b) BF3 (c) 2 NO  (d) All of these 7. Which of the following species is electrophile : (a) OH  (b) 3 CH O   (c) BF3 (d) NH3 8. Acyl cation has two resonating structures (I) and (II)     I II R C O R C O        Which statement is correct for (I) and (II) (a) (I) is more stable than (II) (b) (II) is more stable than (I) (c) Stability of (I) and (II) will be the same (d) For some time (I) will be more stable and for remaining time (II) will be more stable 9. Tautomerism is shown by (a) 3 2 3 O O | | | | CH C CH C CH     (b) 3 2 2 5 O O | | | | CH C CH COOC H    (c) 3 2 CH CH N   O O (d) All of these 10. Which one of the following compounds has maximum enol content in solution (a) 3 2 2 5 O || CH C CH COOC H    (b) 3 2 O || CH C CH CN    (c) 3 3 O || CH C CH   (d) O 11. Which one of the following has the highest nucleophilicity (a) F– (b) OH– (c) CH 3  (d) – NH2 12. The most stable free radical is : (a) 3 2 CH CH  (b) 2 2 CH CH CH   (c) 3 3 CH CH CH   (d) 3 CH 13. +R effect will be shown by : (a) NO2 (b) —CN (c) CHO (d) – NHCOCH3
  • 7. Chemistry : General Organic Chemistry & Isomerism 14. The number of delocalised  -electrons in the given compound is  (a) 4 (b) 6 (c) 8 (d) 2 15. In pyridine : N : Number of conjugated electrons are ; (a) 6 (b) 8 (c) Zero (d) 5 16. Consider the following isomeric alkanes (1) n-pentane (2) Isopentane (3) Neopentane Arrange bp of these compounds in decreasing order : (a) 1 > 2 > 3 (b) 3 > 2 > 1 (c) 1 > 3 > 2 (d) 3 > 1 > 2 17. In which of the following structures the pair of carbon atoms do not lie in the same plane (a) H C 3 C == C CH3 H CH _ H C 3 2 * * (b) CH3 * * (c) CH ==C * * H H (d) H C 3 C == C H CH _ CH 2 3 * * H C 3 18. In which of the following molecules all the effects namely inductive, mesomeric and hyperconjugation operate (a) (b) 3 COCH 3 CH (c) 3 CH 3 CH (d) 19. Most acidic hydrogen is present in (a) O O (b) O (c) (CH3 CO)3 CH (d) None of these 20. Which one of the following chlorides gives white precipitate with AgNO3 most readily (a) CH3 = CH – CH2 Cl (b) CH2 = CH– Cl (c) CH3 – CH2 – CH2 Cl (d) (C6 H5 )2 CH – Cl
  • 8. Chemistry : General Organic Chemistry & Isomerism SECTION - III MULTIPLE CHOICE QUESTIONS 1. Carbanion (X) loses a leaving group to form alkene which is/are correct statements? CH3 CH3 C H3 C H3 H L H , I   CH3 CH3 C H3 C H3 L L II     CH3 C H3 CH3 C H3 (a) It is E2 type (b) It is E1 type (c) It is E1-CB type (d) Step I is fast and II is slow 2. In which case/cases SE will be in meta position? (a) N2 (b) NH C O CH3 (c) N(CH3)3 (d) CF3 3. Which of the following cannot undergo nucleophilic substitution under ordinary condition? (a) Benzyl chloride (b) Allyl chloride (c) Vinyl chloride (d) n-Propyl chloride 4. HCN and HNC are which type of isomers? (a) Position (b) Chain (c) Tautomers (d) Functional 5. Which is/are correct statements for A B (a) A is Z and B is E (b) A and B are same structures (c) A is cis and B is trans (d) A is R and B is S 6. Which of the following is an optically active compound? (a) 1, 3-Butadiene (b) Propadiene (c) 2, 3-Pentadiene (d) 1, 3-Pentadiene 7. Which of the following will show geometrical isomerism? (a) HO—N==N—OH (b) CH3 CH2 NO2 (c) (d) C NOH C H3 C H3
  • 9. Chemistry : General Organic Chemistry & Isomerism 8. Which of the following pairs of compounds are tautomers? (a) Propanal and propanone (b) 1-Propanol and 2-Propanol (c) Ethanol and vinyl alcohol (d) Vinyl alcohol and ethanal 9. Geometric isomerism will be exhibited by (a) 1-Pentene (b) 3-Methyl-1-butene (c) 2-Pentene (d) All of these compounds 10. Which of the following compounds is not chiral? (a) DCH2 CD2 CH2 Cl (b) 3 2 CH CH CH—Cl | D (c) CH3 CHDCH2 Cl (d) CH3 CHCl·CH2 D
  • 10. Chemistry : General Organic Chemistry & Isomerism MISCELLANEOUS QUESTIONS SECTION - IV COMPREHENSION TYPE QUESTIONS Write up - I Isomers which are nonsuper-imposable mirror images of each other are called enantiomers. All optically active compounds exhibit enantiomerims. The stereoisomers which are not mirror images of each other are called diastereomers. Enantiomers are always chiral molecules wheres diastereomers may or may not be chiral, configuration of the compound having no element of symmetry is always chiral. Chiral molecule may or may not contain chiral carbon. 1. Which of the following compounds are chiral? (a) 2 CHO | H —C — OH | CH OH (b) C C H C H3 C C2H5 H (c) Br Cl C CH3 H (d) all of these 2. Which of the following pairs are diastereomers? (a) 3 3 CHO CHO | | H —C —OH and HO —C — H | | CH CH (b) H C COOH C Br Br H C6H5 Br C COOH C H H Br C6H5 and (c) C C H CH3 C H3 H C C CH3 H C H3 H and (d) all of these 3. Which statement is correct for enantiomers : (a) Both are non-superimposable mirror images (b) Both are superimposable mirror images (c) Physical properties are different (d) Reaction velocity with optically active compound is same
  • 11. Chemistry : General Organic Chemistry & Isomerism Write up - II Delocalisation of electrons take place in alternate single and multiple bonds involving carbon atoms. Delocalisation may also occur in a conjugated system involving carbon atom and atom other than the carbon. There are also examples in which pi orbital and p orbital (vacant or half-filled or filled) overlap. Thus delocalisation are of the following types : (i) delocalisation by ,  overlap (ii) delocalisation by , p overlap Delocalisation makes system stable. More is the number of resonating structures more is the stability of the system. 4. In which of the following compounds delocalisation is not possible (a) 1, 4-pentadiene (b) 1, 3-butadiene (c) 1, 3, 5-hexatriene (d) benzene 5. Arrange the following resonating structures of formic acid in decreasing order of stability. (I) O || H —C —O — H (II) O | H —C O— H    (III) O | H —C—OH   (IV) O | H —C—OH   (a) I > II > IV > III (b) I > II > III > IV (c) IV > III > II > I (d) I > IV > II > III 6. Which one of the following carbocation is most stable due to the resonance? (a) (b) 6 5 2 C H — CH  (c) 6 5 6 5 C H — CH — C H  (d) 6 5 6 5 3 C H —C —C H | CH 
  • 12. Chemistry : General Organic Chemistry & Isomerism MULTIPLE MATCHING TYPE QUESTIONS Match the following 7. Column A Column B (A) CH2 =CH2 + HBr in presence of oxygen (1) Carbocation (B) Dehydrobromination of 2-methyl-2-bromopropane (2) Carbanion (C) Alkaline hydrolysis of chloroform (3) Free radical (D) Rearrangement not possible in (4) Carbene (A) (B) (C) (D) (a) 1, 3 2 3, 4 2 (b) 2, 3 1, 3 4 3 (c) 1, 4 3 2 1 (d) 3 1 4 2, 3, 4 8. Column A Column B (A) sp (1) Carbocation (B) sp2 (2) Carbanion (C) sp3 (3) Free radical (D) Both sp2 and sp3 (4) Triplet carbene (A) (B) (C) (D) (a) 2 2 3, 4 1 (b) 2 2, 3, 4 2 1 (c) 3 2, 3, 4 1 2 (d) 4 3 2 1 9. Column A Column B (A) C6 H5 CH2 CD2 Br on reacting with C2 H5 O– gives C6 H5 —CH==CD2 (1) E1 (B) PhCHBrCH3 and PhCHBrCD3 both react with the same rate. (2) E2 (C) C6 H5 CH2 CH2 Br on treatment with C2 H5 O– and C2 H5 OD gives C6 H5 CD==CH2 (3) E1CB (D) C6 H5 CH2 CH2 Br reacts faster than C6 H5 CD2 CH2 Br on reaction with C2 H5 O– in ethanol (4) First order reaction
  • 13. Chemistry : General Organic Chemistry & Isomerism (A) (B) (C) (D) (a) 1, 4 2 3 2, 3 (b) 2 1, 4 3 2 (c) 2 1, 4 1, 3 2, 3 (d) 1, 4, 2, 3 3 2 ASSERTION-REASON TYPE QUESTIONS The question given below consist of an ASSERTION and the REASON. Use the following key for the appropriate answers (a) If both Assertion and Reason are correct and Reason is the correct explanation for Assertion (b) If both Assertion and Reason are correct and Reason is not the correct explanation for Assertion (c) If Assertion is correct but Reason is not correct. (d) If Assertion is incorrect but Reason is correct. 10. Assertion : Cyclobutane is more reactive than cyclopentane. Reason : The carbocyclic ring in cyclobutane is more strained than in cyclopentane. 11. Assertion : SN 1 reaction of 2-chloro-3, 3-dimethylbutane with NaOH gives 2, 3-dimethyl-2-butanol as the major product. Reason : Intermediate is a secondary carbocation which undergoes 1, 2-methyl shift giving more stable tertiary carbocation. 12. Assertion : Hyperconjugation results in thestabilisationo f carbocation by delocalising the positive charge. Reason : Hyperconjugation produces some additional bonding between the electron-deficient carbon and the adjacent carbon. 13. Assertion : Ortho-hydroxy benzoic acid is much more acidic than benzoic acid. Reason : Anion formed from ortho-hydroxy benzoic acid is stabilised by hydrogen bonding. 14. Assertion : The carbocation CF3 —C+ H2 is less stable than C+ F3 . Reason : In case of CF3 —C+H 2, CF3 is strong electron withdrawing therefore increases +ve charge when in C+F3, Ione pair of F overlap with vacant p-orbital of carbon reducing +ve change by p-pt bonding or back bonding. 15. Assertion : The Friedel craft alkylation of nitrobenzene gives meta alkylated nitrobenzene. Reason : Nitrogroups an meta directing.
  • 14. Chemistry : General Organic Chemistry & Isomerism SECTION - V (PROBLEMS ) A. Only one option is correct (Objective Questions) 1. Among the following, the least stable resonance structure is (a) N O O (b) N O O (c) N O O (d) N O O 2. The IUPAC name of C6 H5 COCl is : (a) Benzoyl chloride (b) Benzene chloro ketone (c) Benzene carbonyl chloride (d) Chloro phenyl ketone 3. 4-methyl benzene sulphonic acid reacts with sodium acetate to give : (a) CH3 SO3Na ; CHCOOH (b) COONa CH3 ; SO3 (c) CH3 ; SO3 (d) O2S CH3 OCOCH3 ; NaOH 4. Which of the following resonating structures of 1-methyoxy-1, 3-butadiene is least stable? (a) 2 3 CH — CH CH — CH O— CH     (b) 2 2 3 CH CH — CH — CH O— CH     (c) 2 3 CH — CH — CH CH — O — CH    (d) 2 3 CH CH — CH — CH — O — CH   
  • 15. Chemistry : General Organic Chemistry & Isomerism 5. Arrange in order of increasing acidic strength N + H3 H3N + COOH Z X Y (a) X > Z > Y (b) Z < X > Y (c) X > Y > Z (d) Z > X > Y 6. C2 is rotated anticlockwise 120°C about C2 —C3 bond. The resulting conformer is : CH3 H H H CH3 H 3 2 (a) partially eclipsed (b) eclipsed (c) gauche (d) staggered 7. Among the following the molecule with the highest dipole moment is : (a) CH3 Cl (b) CH2 Cl2 (c) CHCl3 (d) CCl4 8. Which of the following represent the given mode of hybridization sp2 – sp2 – sp – sp from left to right? (a) H2 C==CH—CCH (b) HCC—C—CCH (c) H2 C==C==C==CH2 (d) C H2 CH2 9. Which of the following hydrocarbons has the lowest dipole moment? (a) C C H CH3 C H3 H (b) CH3 —HC==HC—CH3 (c) CH3 —CH2 CH==CH2 (d) CH2 ==CH—CH==CH2 10. Which of the following compounds exhibits, stereoisomerism? (a) 2-methyl butene-1 (b) 3-methyl butyne-1 (c) 3-methyl butanoic acid (d) 2-methyl butanoic acid
  • 16. Chemistry : General Organic Chemistry & Isomerism B. More than one options are correct (Objective Questions) 1. Only two isomeric monochloro derivatives are possible for : (a) n-butane (b) 2, 4-dimethyl pentane (c) benzene (d) 2-methyl propane 2. The compound in which C uses its sp3 - hybrid orbitals for bond formation is : (a) HCOOH (b) (H2 N)2 CO (c) (CH3 )3 COH (d) CH3 CHO 3. Which of the following have asymmetric carbon atom? (a) H C C H H Cl H Br (b) H C C Cl H H H Cl (c) H C C D H H H Cl (d) H C C CH3 Br H OH H 4. The molecules that will have dipole moment are : (a) 2, 2 dimethyl propane (b) trans 2-pentene (c) cis-3-hexene (d) 2, 2, 3, 3-tetramethyl butane 5. What is the decreasing order of strength of the bases : 2 3 2 OH , NH , H — C C and CH — CH ?      (a) 3 2 2 CH — CH NH H — C C OH         (b) 3 2 2 H — C C CH — CH NH OH         (c) 2 3 2 OH NH H — C C CH — CH         (d) 2 3 2 NH H — C C OH CH — CH         6. Which of the following compounds will show geometrical isomerism? (a) 2-butene (b) propene (c) 1-phenyl propane (d) 2-methyl butene 7. Tautomerism is exhibited by : (a) CH==CH—OH (b) O O (c) O O (d) O O
  • 17. Chemistry : General Organic Chemistry & Isomerism C. Assertion-Reason Type Questions 1. In the following a statement (S) in the left hand column and an explanation (E) in the right hand column. Ascertain the relationship between S and E and select the correct code among a, b, c and d which are defined below : (a) Both S and E are true, and E is the correct explanation of S (b) Both S and E are true, but E is not the correct explanation of S (c) S is true but E is false (d) S is false but E is true Statement (S) : p-Hydroxybenzoic acid has a lower boiling point than o-hydroxybenzoic acid. Explanation (E) :o-Hydroxybenzoic acid has intramolecular hydrogen bonding. SUBJECTIVEQUESTIONS 1. Write the IUPAC name of CH3CH2CH==CH·COOH 2. Give the IUPAC name of the following compound : Me Me Me Me Me (Me = methyl) 3. Write the IUPAC name for the following : C H3 N C CH2 CH3 CH3 C2H5 CH3 4. Write tautomeric forms of phenol. 5. Draw the setreochemical structures of the products in the following reactions : (i) Br H C2H5 C2H5 2 N NaOH S   (ii) 2 H Lindlar catalyst R — C C — R   6. Write down the structures of the stereoisomers formed when cis-2-butene is reacted with bromine. 7. Discuss the hybridization of carbon atoms in alkene (C3H4) and show the -orbital overlaps.
  • 18. Chemistry : General Organic Chemistry & Isomerism 8. Identify the pairs of enantiomers and diastereomers from the following : H OH CH3 O H H CH3 I O H H CH3 O H H CH3 II O H H CH3 H OH CH3 III 9. (a) Draw Newmann’s projection for the less stable staggered form of butane. (b) Relatively less stability of the staggered form is due to : (i) Torsional strain (ii) van der Waal’s strain (iii) Combination of the above two 10. obs ix    l where l is the dipole moment of stable conformer and xi is the mole fraction of that conformer. . (a) Write stable conformer for Z—CH2—CH2—Z in Newmann’s projection. If µsolution = 1.0 D and mole fraction of anti form = 0.82, find µGauche (b) Write most stable meso conformer of CHDY | CHDY If (i) Y = CH3 about C2—C3 rotation and (ii) Y = OH about C! —C2 rotation.
  • 19. Chemistry : General Organic Chemistry & Isomerism ANSWERS EXERCISE - 1 1. (3 Cyano Propanal) 2. (3 Ethyl 2, 5 di Methyl hexane) 3. (2, 3 dipoxy pentane) 4. (3 Chloro Pentanidoi Acid) EXERCISE - 2 1. (4) 2. (4) 3. (2) 4. (3) 5. (2) EXERCISE - 3 1. (3) 2. (2) 3. (1) 4. (4) 5. (3) 6. (2) EXERCISE - 4 1. (a) C6H5 + is a vinyl carbocation and is less stable than C6H11 + , a 2° carbocation. (b) In C6 H5 : – , the electron pair is in an sp2 hybrid orbital. The carbanion has more s-character and is more stable than C6 H11 : – whose unshared electron pair is in an sp3 hybrid orbital. EXERCISE - 5 1. (a) There are four stereoisomers. A and B are enantiomers, are are C and D. (b) A and B are diastereomers of C and D. CH3 C H5 2 Cl H HO H CH3 C H5 2 H Cl H OH (A) (B) (racemate)1 CH3 C H5 2 Cl H H HO CH3 C H5 2 H Cl HO H (C) (D) (racemate)2 2. Cyclopentane is best considered as a flat ring. All trans-isomers exist as a pair of enantiomers. All cis- isomers are meso.
  • 20. Chemistry : General Organic Chemistry & Isomerism Me Me Me Me racemate trans–1, 2-Dimethylcyclopentane Me Me meso cis –1, 2-Dimethylcyclopentane Me Me Me Me racemate trans–1, 3-Dimethylcyclopentane meso cis –1, 3-Dimethylcyclopentane Me Me + C H 6 5 + + C H 6 11 + H – C H 6 5: – sp 2 C H 6 11: – H – sp 3 SECTION - I (Subjective Questions) Answers are given in the separate booklet (Level – I to Level – III) SECTION - II (Single Choice Questions) 1. (c) 2. (a) 3. (d) 4. (d) 5. (a) 6. (d) 7. (c) 8. (b) 9. (d) 10. (d) 11. (c) 12. (b) 13. (d) 14. (b) 15. (a) 16. (a) 17. (d) 18. (b) 19. (c) 20. (d)
  • 21. Chemistry : General Organic Chemistry & Isomerism SECTION - III (Multiple Choice Questions) 1. (c, d) 2. (c, d) 3. (d) 4. (c, d) 5. (a, c) 6. (c) 7. (a, b, c) 8. (d) 9. (c) 10. (a) SECTION - IV (Comprehension Type Questions) 1. (d) 2. (c) 3. (a) 4. (a) 5. (b) 6. (d) (Multiple Matching Type Questions) 7. (d) 8. (b) 9. (b) (Assertion Reason Type Questions) 10. (b) 11. (a) 12. (a) 13. (a) 14. (a) 15. (d) SECTION - V A. Only one option is correct (Objective Questions) 1. (a) 2. (c)
  • 22. Chemistry : General Organic Chemistry & Isomerism 3. (a) 4. (c) 5. (a) 6. (c) 7. (a) 8. (a) 9. (b) 10. (d) C. Assertion-reason type questions 1. (d) SUBJECTIVE Answers are given in the separate booklet.