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General Organic Chemistry-03 - Assignments (New)
General Organic Chemistry-03 - Assignments (New)
ASSIGNMENTS
SECTION - I
SUBJECTIVE QUESTIONS
LEVEL - I
1. Give the IUPAC name for the amine.
CH3
|
CH3 —N —C — CH 2CH 3
| |
CH3 C2H5
2. Write the aci-form of nitromethane.
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
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 :
NH 2
C
H3C
COOH
H3C
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 OH
(a) C and C
H CH3
HO C 2 H5
C 2 H5 H
CH 2 Br H
(b) C and C
OH CH3
H HO
CH3 CH2 Br
(c) C6 H 5 C H C6 H5 (d) CH3 C H CH 3
9. Identify the pairs of enantiomers and diastereomers amongst the following compounds
H CH3 OH
(a) (b) (c)
Chemistry : General Organic Chemistry & Isomerism
H H
CH3 H H CH3
H H
LEVEL - III
1. Arrange the following in increasing order of acidic strength
OCH3
OCH3
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 CH2Cl CH2Cl
N N N N
H H H
CH3
H OH
9. The configuration of the chiral centre of the given compound is 2s, 3s explain.
Br H
Et
Chemistry : General Organic Chemistry & Isomerism
10. Pick out the compound which can be obtained is an optically active from.
COOH
NO2 HOOC
H OH
H3C H
, , HO H
H COOH H OH
NO2 HOOC
COOH
COOH O N
2
NO2 HOOC
Chemistry : General Organic Chemistry & Isomerism
SECTION - II
SINGLE CHOICE QUESTIONS
1. Consider the following carbanions :
(1) CH 3 C H 2 (2) CH 2 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) CH 2 C H (b) CH 3 C H 2
(c) CH 2 CH C H 2 (d) C 6 H 5 C H 2
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 :
NH2 NH2
(a) (b)
NO2
NH2 NH2
(c) (d)
CN CH3
4. Consider the following compounds :
(1) (2)
N N
H
O O
(3) (4)
N N N N
H H H
(4)
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
O
||
(c) CH 3 C CH 3 (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) CH 3 C H 2 (b) CH 2 CH C H 2
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
* *
H3C CH3 CH3
(a) C == C (b)
CH3 _ H2*C H *
CH2 _ CH3
H *
* H3C
CH ==C C == C
(c) H (d) H
H3C
* *
18. In which of the following molecules all the effects namely inductive, mesomeric and hyperconjugation
operate
CH 3
(c) CH 3 (d)
CH 3
19. Most acidic hydrogen is present in
O
O O
(a) (b)
SECTION - III
MULTIPLE CHOICE QUESTIONS
1. Carbanion (X) loses a leaving group to form alkene which is/are correct statements?
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
H3C
(c) (d) C NOH
H3C
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.
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.
O O
|| |
(I) H —C — O — H (II) H —C O— H
O O
| |
(III) H — C— OH (IV) 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) C6 H5 — C H 2
(c) C6 H 5 — C H — C6 H 5 (d) C6 H 5 —C — C6 H5
|
CH3
Chemistry : General Organic Chemistry & Isomerism
SECTION - V
(PROBLEMS )
O O
(a) N (b) N
O O
O O
(c) N (d) N
O O
CH3 COONa
SO3Na CH 3
O2 S OCOCH3
CH 3 CH3
+ +
H3 N N H3
Z Y
COOH
X
CH3
H H
3
2
H H
CH3
H3C CH3
(a) C C (b) CH3—HC==HC—CH3
H H
(c) CH3 —CH2CH==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
Cl Br H Cl
(a) H C C H (b) H C C Cl
H H H H
H Cl H H
H H Br OH
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 :
OH , NH 2 , H — C C and CH3 — CH 2 ?
(a) CH3 — CH 2 NH 2 H — C C OH
(b) H — C C CH 3 — CH 2 NH 2 OH
(c) OH NH 2 H — C C CH 3 — CH 2
(d) NH 2 H — C C OH CH 3 — CH 2
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 :
(c) O (d) O
O O
Chemistry : General Organic Chemistry & Isomerism
SUBJECTIVE QUESTIONS
1. Write the IUPAC name of CH3CH2CH==CH·COOH
2. Give the IUPAC name of the following compound :
Me
Me Me
(Me = methyl)
Me Me
CH3
CH3 C 2 H5
C 2 H5
NaOH
(i) Br H
S
N2
C 2 H5
H2
(ii) R — C C — R
Lindlar catalyst
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 (C 3H4) and show the -orbital overlaps.
Chemistry : General Organic Chemistry & Isomerism
H OH HO H HO H
HO H HO H H OH
I II 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 i x l
where l is the dipole moment of stable conformer and x i is the mole fraction of that conformer..
(a) Write stable conformer for Z—CH 2—CH2—Z in Newmann’s projection.
If µ solution = 1.0 D and mole fraction of anti form = 0.82, find µ Gauche
CHDY
(b) Write most stable meso conformer of |
CHDY
If (i) Y = CH3 about C 2—C 3 rotation and
(ii) Y = OH about C ! —C 2 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 C6H5: –, the electron pair is in an sp2 hybrid orbital. The carbanion has more s-character and is
more stable than C6H11: – 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.
(racemate)1 (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 Me Me
racemate meso
trans–1, 2-Dimethylcyclopentane cis –1, 2-Dimethylcyclopentane
Me Me Me Me
Me Me
racemate meso
trans–1, 3-Dimethylcyclopentane cis –1, 3-Dimethylcyclopentane
3
2 sp
+ H – sp H
+ –
+ + – –
C6H5 C6H11 C6H5: C6H11:
SECTION - I
(Subjective Questions)
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)
SECTION - V
3. (a) 4. (c)
5. (a) 6. (c)
7. (a) 8. (a)
9. (b) 10. (d)
SUBJECTIVE
Answers are given in the separate booklet.