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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