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Ms Chouhan & Team: Organic Chemistry

This document contains a practice test for organic chemistry with multiple choice questions. It covers topics like hyperconjugation, heat of combustion/hydrogenation of alkene isomers, C=C bond lengths, and inductive effects. There are 14 questions in total with an answer key provided.

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Prithviraj Ghosh
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0% found this document useful (0 votes)
4K views16 pages

Ms Chouhan & Team: Organic Chemistry

This document contains a practice test for organic chemistry with multiple choice questions. It covers topics like hyperconjugation, heat of combustion/hydrogenation of alkene isomers, C=C bond lengths, and inductive effects. There are 14 questions in total with an answer key provided.

Uploaded by

Prithviraj Ghosh
Copyright
© © All Rights Reserved
We take content rights seriously. If you suspect this is your content, claim it here.
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Download as PDF, TXT or read online on Scribd
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ORGANIC CHEMISTRY : MS CHOUHAN & TEAM TIME : 35 MIN.

DPP-81
1. Hyperconjugation is possible in
(A) alkenes (B) alkynes (C) carbocations (D) all of these
2. Hyperconjugation is possible in
(A) Free radicals (B) Carbanions (C) Alcohols (D) Amines
3. Hyperconjugation occurs in

(A) CH3–CH=CH2 (B) CH3–CH2–CH=CH2 (C) (D) all of these

4. Hyperconjugation occurs in

(A) (B) CH3–CH=CH–CH3 (C) Ph–CH=CH2 (D)  CH3

5. Hyperconjugation occurs in

(A) (B) (C) (D)

6. Hyperconjugation occurs in


CH2
(A) (B)

(C) (D) all of these

7. Hyperconjugation occurs in

 
(A) C H3 (B) CH3 – C H2 (C) (D) both (B) and (C)

8.

How many hyperconjugable H-atoms does this alkene has?


(A) 10 (B) 6 (C) 12 (D) 15

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9.

How many hyperconjugable H-atoms does this radical has?


(A) 5 (B) 6 (C) 12 (D) 8

10.

Canonical structures due to hyperconjugation in this molecule can be written as

HB HA HA

O –
O –
O
(A) C = CH – CH2 C = CH – CH2 C = CH – CH2
HC HO
A HC O
HB HB HO
C

HB HA HA
O O O
(B) C = CH – CH2 C = CH – CH2 C = CH – CH2

HC –
HO
A
HC –
O
HB HB HCO

(C) both (A) and (B) (D) none of these

CH3 CH3 CH3

11.
CH3 CH3 CH3
(I) (II) (III)

Among these compounds, which of the following orders is correct for their nobond-resonance energy?
(A) III > II > I (B) I > II > III (C) I > III > II (D) II > III > I

12. Compound Homolytic bond


dissociation energy
 
CH4  C H3  H 104 Kcal/mol

92 Kcal/mol

Notice the homolytic bond-dissociation energy of the alkanes. Now, ignoring the contribution of inductive
effect, no-bond-resonance energy of tert-butyl radical can be calculated to be
(A) 6 Kcal/mol (B) 10 Kcal/mol (C) 12 Kcal/mol (D) 14 Kcal/mol

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13.

Among these cycloalkenes, which of the following orders of stability is correct?


(A) I > II > III (B) III > II > I (C) II > I > III (D) II > III > I

14.

Among these dienes, which of the following orders of stability is correct?


(A) I > II > III (B) III > II > I (C) II > III > I (D) II > I > III

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ANSWER KEY
1. D 2. A 3. D 4. B 5. B
6. C 7. D 8. A 9. A 10. A
11. A 12. C 13. D 14. B

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ORGANIC CHEMISTRY : MS CHOUHAN & TEAM TIME : 35 MIN. DPP-82

1.

Which of the following statements is correct, about these cycloalkenes?


(A) Stability difference between I and II is more than that between III and IV
(B) Stability difference between I and II is less than that between III and IV
(C) Overall, stability order is I > II > III > IV
(D) none of these

2.
CH2  CH – C  C – CH  CH2
II

Which of the following orders is correct for heat of combustion of these isomers?
(A) I > II (B) II > I (C) I = II (D) Not predictable

3.

Which of the following order is correct for heat of combustion of these isomers?
(A) I > II > III (B) III > II > I (C) II > III > I (D) I > III > II

4.

Which of the following orders is correct for heat of hydrogenation of these compounds?
(A) I > II > III (B) III > II > I (C) II > I > III (D) I > III > II

5.

Which of the following orders is correct for heat of hydrogenation of these compounds?
(A) I > II > III (B) III > II > I (C) III > I > II (D) II > III > I

6.

Which of the following orders is correct for heat of hydrogenation of these compounds?
(A) I > II > III (B) III > II > I (C) II > III > I (D) I > III > II

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7.

Which of the following orders is correct for heat of hydrogenation of these compounds?
(A) I > II > III (B) III > II > I (C) II > I >III (D) III > I > II

CH3
CH3 CH2
8.
I II
III

Which of the following orders is correct for heat of hydrogenation of these compounds?
(A) I > II > III (B) III > II > I (C) III > I > II (D) II > I > III

CH3

9.
CH3
III

Which of the following order is correct for heat of hydrognenation of these compounds?
(A) I > II > III (B) III > II > I (C) II > III > I (D) III > I > II

CH3
a b
10.
CH3

a and b are the length of these two C=C bonds. Now, which of the following orders is correct?
(A) a = b (B) a > b (C) b > a (D) Not predictable

CH3
a b c
11.
CH3

a, b and c are the length of these C=C bonds. Now, which of the following orders is correct?
(A) a = b = c (B) a > b > c (C) c > b > a (D) b > c > a

12. Inductive effect of -NO2 group operates in

(A) (B) (C) (D) all of these

13. Inductive effect of -CH3 group operates in

CH3 CH3 CH3


(A) (B) (C) (D) both (B) and (C)

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14.

Which of these gorups has +I effect?


(A) I (B) II (C) III (D) all of these

15.

Hybridization of the negatively charged C-atom of this anion is


(A) sp3 (B) sp2 (C) sp (D) unhybridized

16.

Which of the following orders is correct for heat of combustion of these isomeric alkenes?
(A) I > II > III (B) III > II > I (C) III > I > II (D) II > III > I

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ANSWER KEY
1. A 2. B 3. C 4. A 5. D
6. C 7. A 8. A 9. C 10. C
11. C 12. D 13. D 14. D 15. B
16. D

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ORGANIC CHEMISTRY : MS CHOUHAN & TEAM TIME : 35 MIN. DPP-83

1.

Empty orbital of this carbocation is


(A) 2p (B) sp3 (C) sp2 (D) sp
2. Negative charge of which of the following carbanions is not resonance-stabilized?

(A) (B) (C) (D)

3.

Which of the following orders is correct for the stability of these carbocations?
(A) I > II > III (B) III > II> I (C) I > III > II (D) II > III > I

4.

Which of the following orders is correct for the stability of these carbocations?
(A) I > II > III (B) III > II > I (C) II > I > III (D) II > III > I

5.

Which of the following orders is correct for the stability of these carbocations?
(A) I > II > III (B) III > II > I (C) II > I > III (D) II > III > I

6.

Which of the following orders is correct for the stability of these carbocations?
(A) I > II > III (B) III > II > I (C) I > III > II (D) II > I > III

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7.

Which of the following orders is correct for the stability of these carbanions?
(A) I > II > III (B) III > II > I (C) II > I > III (D) I  II  III

O–
CH2
8.

III

Which of the following orders is correct for the stability of these carbanions?
(A) I > II > III (B) III > II > I (C) II > III > I (D) II > I > III


O –
O –
O
(I) (II) (III)
9.
CH3 Cl

Which of the following orders is correct for the stability of these carbanions?
(A) I > II > III (B) III > II > I (C) III > I > II (D) II > III > II


O –
O –
O
Cl
10. (I) (II) (III)
Cl
Cl

Which of the following orders is correct for the stability of these carbanions?
(A) I > II > III (B) III > II > I (C) II > I > III (D) II > III > I

“Every great man tasted the bitter pills of


failure but they never swallowed them.”

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ANSWER KEY
1. C 2. C 3. A 4. C 5. B
6. C 7. A 8. B 9. C 10. A

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ORGANIC CHEMISTRY : MS CHOUHAN & TEAM TIME : 35 MIN. DPP-84

1. In each of the following groups of compounds, identify the one with the largest heat of combustion and the
one with the smallest. In which cases can a comparison of heats of combustion be used to assess relative
stability ?
(a) Cyclopropane, cyclobutane, cyclopentane

(b) cis-1,2-Dimethylcyclopentane, methylcyclohexane, 1,1,2,2-tetramethylcyclopropane

(c)

H H
H
(d)

H H H

2. Write a balanced chemical equation for the combustion of each of the following compounds :
(a) Decane

(b) Cyclodecane

(c) Methylcyclononane

(d) Cyclopentylcyclopentane

3. In each of the following groups of compounds, identify the one with the largest heat of combustion and the
one with the smallest. (Try to do this problem without consulting Table).
(a) Hexane, heptane, octane
(b) Isobutane, pentane, isopentane
(c) Isopentane, 2-methylpentane, neopentane
(d) Pentane, 3-methylpentane, 3,3-dimethylpentane
(e) Ethylcyclopentane, ethylcyclohexane, ethylcycloheptane

4. Match each alkene with the appropriate heat of combustion :


Compound Heats of combustion (kJ/mol)
(a) 1-Heptene (p) 5293
(b) 2,4-Dimethyl-1-pentene (q) 4658
(c) 2,4-Dimethyl-2-pentene (r) 4650
(d) (Z)-4,4-Dimethyl-2-pentene (s) 4638
(e) 2,4,4-Trimethyl-2-pentene (t) 4632

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5. Choose the more stable alkene in each of the following pairs Explain your reasoning.
(a) 1-Methylcyclohexene or 3-methylcyclohexene

(b) Isopropenylcyclopentane or allylcyclopentane

(c) or

Bicyclo[4.2.0]oct-7-ene Bicyclo[4.2.0]oct-3-ene

(d) (Z)-Cyclononene or (E)-cyclonoene

(e) (Z)-Cyclooctadecene or (E)-cyclooctadecene

6. (a) Suggest an explanation for the fact that 1-methylcyclopropene is some 42 kJ/mol (10 kcal/mol) less
stable than methylenecyclopropane.

(b) On the basis of your answer to part (a), compare the expected stability of 3-methyl-cyclopropene with
that of 1-methylcyclopropene and that of methylenecyclopropane.

7. What three alkenes yield 2-methylbutane on catalytic hydrogenation ?

8. Match the following alkenes with the appropriate heats of hydrogenation :


Compound Heats of hydrogenation in kJ/mol :
(a) 1-Pentene (p) 151
(b) (E)-4,4-Dimethyl-2-pentene (q) 122
(c) (Z)-4-Methyl-2-pentene (r) 114
(d) (Z)-2,2,5,5-Tetramethyl-3-hexene (s) 111
(e) 2,4-Dimethyl-2-pentene (t) 105

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ANSWER KEY
1. (a) c > b > a (b) c > a > b (c) b > a > c (d) b > c > a

 y y
2. CxHy +  x   O2  x CO2 + H2O
 4 2

3. (a) c > b > a (b) b > c > a (c) b > a > c (d) c > b > a (e) c > b > a
4. (a)  q, (b)  s, (c)  t, (d)  r, (e)  p
5. (a) a > b (b) a > b (c) b > a (d) Z > E (e) E > Z

6. (a) -bond in 3-memberd ring is unstable (b) Stability order : 3 > 2 > 1

7.

8. (a)  q, (b)  r, (c)  s, (d)  p, (e)  t

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