01. Resonance
GENERAL ORGANIC CHEMISTRY

231671 $\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{Cl}$ undergoes homolytic fission, produces

1 $\mathrm{CH}_{3} \dot{\mathrm{C}} \mathrm{H}_{2}$ and $\dot{\mathrm{C}} \mathrm{l}$
2 $\mathrm{CH}_{3} \stackrel{\oplus}{\mathrm{C}} \mathrm{H}_{2}$ and $\mathrm{Cl}^{-}$
3 $\mathrm{CH}_{3} \stackrel{\oplus}{\mathrm{C}} \mathrm{H}_{2}$ and $\dot{\mathrm{C}} \mathrm{l}$
4 \(\mathrm{CH}_3 \dot{\mathrm{C}} \mathrm{H}_2\) and \(\mathrm{Cl}^{-}\)
GENERAL ORGANIC CHEMISTRY

231672 $\mathrm{C}-\mathrm{C}$ bond order in benzene is

1 1
2 2
3 between 1 and 2
4 None of these
GENERAL ORGANIC CHEMISTRY

231675 Relative stabilities of the following carbocation will be in order-
original image

1 IV $<$ III $<$ II $<$ I
2 IV $<$ II $<$ III $<$ I
3 II $<$ IV $<$ III $<$ I
4 I $<$ II $<$ III $<$ IV
GENERAL ORGANIC CHEMISTRY

231676 Consider the following sequence of reactions,
\(=\,\,-\,\overset{\star }{\mathop{\text{C}}}\,{{\text{H}}_{2}}\text{OH}\xrightarrow{\text{HBr}}A\xrightarrow{{{\text{O}}_{3}}/\text{ reduction }}B+C\)

1 \(=\,{{-}^{\star }}\text{C}{{\text{H}}_{2}}\text{Br}\,\,\,\,\,\,\text{C}{{\text{H}}_{2}}=\text{O}\quad \text{O}=\text{CH}-\overset{\star }{\mathop{\text{C}}}\,{{\text{H}}_{2}}\text{Br}\)
2 \(^{\star }=\,-\text{C}{{\text{H}}_{2}}\text{Br}\,\,\,\,\,\,\overset{\star }{\mathop{\text{C}}}\,{{\text{H}}_{2}}=\text{O}\quad \text{O}=\text{CH}-C{{\text{H}}_{2}}\text{Br}\)
3 \({{=}^{\star }}\,-\text{C}{{\text{H}}_{2}}\text{Br}\,\,\,\,\,\,\overset{\star }{\mathop{\text{C}}}\,{{\text{H}}_{2}}=\text{O}\quad \text{O}=\text{CH}-C{{\text{H}}_{2}}\text{Br}\)
4 \(^{\star }=\,-\text{C}{{\text{H}}_{2}}\text{Br}\,\,\,\,\,\,\overset{\star }{\mathop{\text{C}}}\,{{\text{H}}_{2}}=\text{O}\quad \text{O}=\text{CH}-\overset{\star }{\mathop{\text{C}}}\,{{\text{H}}_{2}}\text{Br}\)
GENERAL ORGANIC CHEMISTRY

231678 Arrange the following in increasing order of stability on the basis of reasonance.
(i) \(\mathrm{CH}_2=\mathrm{CH}-\mathrm{CH}=\mathrm{CH}-\stackrel{+}{\mathrm{H}}_2\)
(ii) \(\mathrm{CH}_2=\mathrm{CH}-\stackrel{+}{\mathrm{CH}}-\mathrm{CH}=\mathrm{CH}_2\)
(iii) \(\mathrm{CH}_2=\mathrm{CH}-\stackrel{+}{\mathrm{CH}}-\stackrel{-}{\mathrm{C}}-\stackrel{+}{\mathrm{C}}_2\)
(iv) \(\stackrel{+}{\mathrm{CH}}_2-\mathrm{CH}=\mathrm{CH}-\stackrel{-}{\mathrm{CH}}-\stackrel{+}{\mathrm{CH}}_2\)

1 (ii) $>$ (i) $>$ (iii) $>$ (iv)
2 (iii) $>$ (ii) $>$ (i) $>$ (iv)
3 (i) $>$ (iii) $>$ (ii) $>$ (iv)
4 (iv) $>$ (ii) $>$ (iii) $>$ (i)
GENERAL ORGANIC CHEMISTRY

231671 $\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{Cl}$ undergoes homolytic fission, produces

1 $\mathrm{CH}_{3} \dot{\mathrm{C}} \mathrm{H}_{2}$ and $\dot{\mathrm{C}} \mathrm{l}$
2 $\mathrm{CH}_{3} \stackrel{\oplus}{\mathrm{C}} \mathrm{H}_{2}$ and $\mathrm{Cl}^{-}$
3 $\mathrm{CH}_{3} \stackrel{\oplus}{\mathrm{C}} \mathrm{H}_{2}$ and $\dot{\mathrm{C}} \mathrm{l}$
4 \(\mathrm{CH}_3 \dot{\mathrm{C}} \mathrm{H}_2\) and \(\mathrm{Cl}^{-}\)
GENERAL ORGANIC CHEMISTRY

231672 $\mathrm{C}-\mathrm{C}$ bond order in benzene is

1 1
2 2
3 between 1 and 2
4 None of these
GENERAL ORGANIC CHEMISTRY

231675 Relative stabilities of the following carbocation will be in order-
original image

1 IV $<$ III $<$ II $<$ I
2 IV $<$ II $<$ III $<$ I
3 II $<$ IV $<$ III $<$ I
4 I $<$ II $<$ III $<$ IV
GENERAL ORGANIC CHEMISTRY

231676 Consider the following sequence of reactions,
\(=\,\,-\,\overset{\star }{\mathop{\text{C}}}\,{{\text{H}}_{2}}\text{OH}\xrightarrow{\text{HBr}}A\xrightarrow{{{\text{O}}_{3}}/\text{ reduction }}B+C\)

1 \(=\,{{-}^{\star }}\text{C}{{\text{H}}_{2}}\text{Br}\,\,\,\,\,\,\text{C}{{\text{H}}_{2}}=\text{O}\quad \text{O}=\text{CH}-\overset{\star }{\mathop{\text{C}}}\,{{\text{H}}_{2}}\text{Br}\)
2 \(^{\star }=\,-\text{C}{{\text{H}}_{2}}\text{Br}\,\,\,\,\,\,\overset{\star }{\mathop{\text{C}}}\,{{\text{H}}_{2}}=\text{O}\quad \text{O}=\text{CH}-C{{\text{H}}_{2}}\text{Br}\)
3 \({{=}^{\star }}\,-\text{C}{{\text{H}}_{2}}\text{Br}\,\,\,\,\,\,\overset{\star }{\mathop{\text{C}}}\,{{\text{H}}_{2}}=\text{O}\quad \text{O}=\text{CH}-C{{\text{H}}_{2}}\text{Br}\)
4 \(^{\star }=\,-\text{C}{{\text{H}}_{2}}\text{Br}\,\,\,\,\,\,\overset{\star }{\mathop{\text{C}}}\,{{\text{H}}_{2}}=\text{O}\quad \text{O}=\text{CH}-\overset{\star }{\mathop{\text{C}}}\,{{\text{H}}_{2}}\text{Br}\)
GENERAL ORGANIC CHEMISTRY

231678 Arrange the following in increasing order of stability on the basis of reasonance.
(i) \(\mathrm{CH}_2=\mathrm{CH}-\mathrm{CH}=\mathrm{CH}-\stackrel{+}{\mathrm{H}}_2\)
(ii) \(\mathrm{CH}_2=\mathrm{CH}-\stackrel{+}{\mathrm{CH}}-\mathrm{CH}=\mathrm{CH}_2\)
(iii) \(\mathrm{CH}_2=\mathrm{CH}-\stackrel{+}{\mathrm{CH}}-\stackrel{-}{\mathrm{C}}-\stackrel{+}{\mathrm{C}}_2\)
(iv) \(\stackrel{+}{\mathrm{CH}}_2-\mathrm{CH}=\mathrm{CH}-\stackrel{-}{\mathrm{CH}}-\stackrel{+}{\mathrm{CH}}_2\)

1 (ii) $>$ (i) $>$ (iii) $>$ (iv)
2 (iii) $>$ (ii) $>$ (i) $>$ (iv)
3 (i) $>$ (iii) $>$ (ii) $>$ (iv)
4 (iv) $>$ (ii) $>$ (iii) $>$ (i)
GENERAL ORGANIC CHEMISTRY

231671 $\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{Cl}$ undergoes homolytic fission, produces

1 $\mathrm{CH}_{3} \dot{\mathrm{C}} \mathrm{H}_{2}$ and $\dot{\mathrm{C}} \mathrm{l}$
2 $\mathrm{CH}_{3} \stackrel{\oplus}{\mathrm{C}} \mathrm{H}_{2}$ and $\mathrm{Cl}^{-}$
3 $\mathrm{CH}_{3} \stackrel{\oplus}{\mathrm{C}} \mathrm{H}_{2}$ and $\dot{\mathrm{C}} \mathrm{l}$
4 \(\mathrm{CH}_3 \dot{\mathrm{C}} \mathrm{H}_2\) and \(\mathrm{Cl}^{-}\)
GENERAL ORGANIC CHEMISTRY

231672 $\mathrm{C}-\mathrm{C}$ bond order in benzene is

1 1
2 2
3 between 1 and 2
4 None of these
GENERAL ORGANIC CHEMISTRY

231675 Relative stabilities of the following carbocation will be in order-
original image

1 IV $<$ III $<$ II $<$ I
2 IV $<$ II $<$ III $<$ I
3 II $<$ IV $<$ III $<$ I
4 I $<$ II $<$ III $<$ IV
GENERAL ORGANIC CHEMISTRY

231676 Consider the following sequence of reactions,
\(=\,\,-\,\overset{\star }{\mathop{\text{C}}}\,{{\text{H}}_{2}}\text{OH}\xrightarrow{\text{HBr}}A\xrightarrow{{{\text{O}}_{3}}/\text{ reduction }}B+C\)

1 \(=\,{{-}^{\star }}\text{C}{{\text{H}}_{2}}\text{Br}\,\,\,\,\,\,\text{C}{{\text{H}}_{2}}=\text{O}\quad \text{O}=\text{CH}-\overset{\star }{\mathop{\text{C}}}\,{{\text{H}}_{2}}\text{Br}\)
2 \(^{\star }=\,-\text{C}{{\text{H}}_{2}}\text{Br}\,\,\,\,\,\,\overset{\star }{\mathop{\text{C}}}\,{{\text{H}}_{2}}=\text{O}\quad \text{O}=\text{CH}-C{{\text{H}}_{2}}\text{Br}\)
3 \({{=}^{\star }}\,-\text{C}{{\text{H}}_{2}}\text{Br}\,\,\,\,\,\,\overset{\star }{\mathop{\text{C}}}\,{{\text{H}}_{2}}=\text{O}\quad \text{O}=\text{CH}-C{{\text{H}}_{2}}\text{Br}\)
4 \(^{\star }=\,-\text{C}{{\text{H}}_{2}}\text{Br}\,\,\,\,\,\,\overset{\star }{\mathop{\text{C}}}\,{{\text{H}}_{2}}=\text{O}\quad \text{O}=\text{CH}-\overset{\star }{\mathop{\text{C}}}\,{{\text{H}}_{2}}\text{Br}\)
GENERAL ORGANIC CHEMISTRY

231678 Arrange the following in increasing order of stability on the basis of reasonance.
(i) \(\mathrm{CH}_2=\mathrm{CH}-\mathrm{CH}=\mathrm{CH}-\stackrel{+}{\mathrm{H}}_2\)
(ii) \(\mathrm{CH}_2=\mathrm{CH}-\stackrel{+}{\mathrm{CH}}-\mathrm{CH}=\mathrm{CH}_2\)
(iii) \(\mathrm{CH}_2=\mathrm{CH}-\stackrel{+}{\mathrm{CH}}-\stackrel{-}{\mathrm{C}}-\stackrel{+}{\mathrm{C}}_2\)
(iv) \(\stackrel{+}{\mathrm{CH}}_2-\mathrm{CH}=\mathrm{CH}-\stackrel{-}{\mathrm{CH}}-\stackrel{+}{\mathrm{CH}}_2\)

1 (ii) $>$ (i) $>$ (iii) $>$ (iv)
2 (iii) $>$ (ii) $>$ (i) $>$ (iv)
3 (i) $>$ (iii) $>$ (ii) $>$ (iv)
4 (iv) $>$ (ii) $>$ (iii) $>$ (i)
GENERAL ORGANIC CHEMISTRY

231671 $\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{Cl}$ undergoes homolytic fission, produces

1 $\mathrm{CH}_{3} \dot{\mathrm{C}} \mathrm{H}_{2}$ and $\dot{\mathrm{C}} \mathrm{l}$
2 $\mathrm{CH}_{3} \stackrel{\oplus}{\mathrm{C}} \mathrm{H}_{2}$ and $\mathrm{Cl}^{-}$
3 $\mathrm{CH}_{3} \stackrel{\oplus}{\mathrm{C}} \mathrm{H}_{2}$ and $\dot{\mathrm{C}} \mathrm{l}$
4 \(\mathrm{CH}_3 \dot{\mathrm{C}} \mathrm{H}_2\) and \(\mathrm{Cl}^{-}\)
GENERAL ORGANIC CHEMISTRY

231672 $\mathrm{C}-\mathrm{C}$ bond order in benzene is

1 1
2 2
3 between 1 and 2
4 None of these
GENERAL ORGANIC CHEMISTRY

231675 Relative stabilities of the following carbocation will be in order-
original image

1 IV $<$ III $<$ II $<$ I
2 IV $<$ II $<$ III $<$ I
3 II $<$ IV $<$ III $<$ I
4 I $<$ II $<$ III $<$ IV
GENERAL ORGANIC CHEMISTRY

231676 Consider the following sequence of reactions,
\(=\,\,-\,\overset{\star }{\mathop{\text{C}}}\,{{\text{H}}_{2}}\text{OH}\xrightarrow{\text{HBr}}A\xrightarrow{{{\text{O}}_{3}}/\text{ reduction }}B+C\)

1 \(=\,{{-}^{\star }}\text{C}{{\text{H}}_{2}}\text{Br}\,\,\,\,\,\,\text{C}{{\text{H}}_{2}}=\text{O}\quad \text{O}=\text{CH}-\overset{\star }{\mathop{\text{C}}}\,{{\text{H}}_{2}}\text{Br}\)
2 \(^{\star }=\,-\text{C}{{\text{H}}_{2}}\text{Br}\,\,\,\,\,\,\overset{\star }{\mathop{\text{C}}}\,{{\text{H}}_{2}}=\text{O}\quad \text{O}=\text{CH}-C{{\text{H}}_{2}}\text{Br}\)
3 \({{=}^{\star }}\,-\text{C}{{\text{H}}_{2}}\text{Br}\,\,\,\,\,\,\overset{\star }{\mathop{\text{C}}}\,{{\text{H}}_{2}}=\text{O}\quad \text{O}=\text{CH}-C{{\text{H}}_{2}}\text{Br}\)
4 \(^{\star }=\,-\text{C}{{\text{H}}_{2}}\text{Br}\,\,\,\,\,\,\overset{\star }{\mathop{\text{C}}}\,{{\text{H}}_{2}}=\text{O}\quad \text{O}=\text{CH}-\overset{\star }{\mathop{\text{C}}}\,{{\text{H}}_{2}}\text{Br}\)
GENERAL ORGANIC CHEMISTRY

231678 Arrange the following in increasing order of stability on the basis of reasonance.
(i) \(\mathrm{CH}_2=\mathrm{CH}-\mathrm{CH}=\mathrm{CH}-\stackrel{+}{\mathrm{H}}_2\)
(ii) \(\mathrm{CH}_2=\mathrm{CH}-\stackrel{+}{\mathrm{CH}}-\mathrm{CH}=\mathrm{CH}_2\)
(iii) \(\mathrm{CH}_2=\mathrm{CH}-\stackrel{+}{\mathrm{CH}}-\stackrel{-}{\mathrm{C}}-\stackrel{+}{\mathrm{C}}_2\)
(iv) \(\stackrel{+}{\mathrm{CH}}_2-\mathrm{CH}=\mathrm{CH}-\stackrel{-}{\mathrm{CH}}-\stackrel{+}{\mathrm{CH}}_2\)

1 (ii) $>$ (i) $>$ (iii) $>$ (iv)
2 (iii) $>$ (ii) $>$ (i) $>$ (iv)
3 (i) $>$ (iii) $>$ (ii) $>$ (iv)
4 (iv) $>$ (ii) $>$ (iii) $>$ (i)
GENERAL ORGANIC CHEMISTRY

231671 $\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{Cl}$ undergoes homolytic fission, produces

1 $\mathrm{CH}_{3} \dot{\mathrm{C}} \mathrm{H}_{2}$ and $\dot{\mathrm{C}} \mathrm{l}$
2 $\mathrm{CH}_{3} \stackrel{\oplus}{\mathrm{C}} \mathrm{H}_{2}$ and $\mathrm{Cl}^{-}$
3 $\mathrm{CH}_{3} \stackrel{\oplus}{\mathrm{C}} \mathrm{H}_{2}$ and $\dot{\mathrm{C}} \mathrm{l}$
4 \(\mathrm{CH}_3 \dot{\mathrm{C}} \mathrm{H}_2\) and \(\mathrm{Cl}^{-}\)
GENERAL ORGANIC CHEMISTRY

231672 $\mathrm{C}-\mathrm{C}$ bond order in benzene is

1 1
2 2
3 between 1 and 2
4 None of these
GENERAL ORGANIC CHEMISTRY

231675 Relative stabilities of the following carbocation will be in order-
original image

1 IV $<$ III $<$ II $<$ I
2 IV $<$ II $<$ III $<$ I
3 II $<$ IV $<$ III $<$ I
4 I $<$ II $<$ III $<$ IV
GENERAL ORGANIC CHEMISTRY

231676 Consider the following sequence of reactions,
\(=\,\,-\,\overset{\star }{\mathop{\text{C}}}\,{{\text{H}}_{2}}\text{OH}\xrightarrow{\text{HBr}}A\xrightarrow{{{\text{O}}_{3}}/\text{ reduction }}B+C\)

1 \(=\,{{-}^{\star }}\text{C}{{\text{H}}_{2}}\text{Br}\,\,\,\,\,\,\text{C}{{\text{H}}_{2}}=\text{O}\quad \text{O}=\text{CH}-\overset{\star }{\mathop{\text{C}}}\,{{\text{H}}_{2}}\text{Br}\)
2 \(^{\star }=\,-\text{C}{{\text{H}}_{2}}\text{Br}\,\,\,\,\,\,\overset{\star }{\mathop{\text{C}}}\,{{\text{H}}_{2}}=\text{O}\quad \text{O}=\text{CH}-C{{\text{H}}_{2}}\text{Br}\)
3 \({{=}^{\star }}\,-\text{C}{{\text{H}}_{2}}\text{Br}\,\,\,\,\,\,\overset{\star }{\mathop{\text{C}}}\,{{\text{H}}_{2}}=\text{O}\quad \text{O}=\text{CH}-C{{\text{H}}_{2}}\text{Br}\)
4 \(^{\star }=\,-\text{C}{{\text{H}}_{2}}\text{Br}\,\,\,\,\,\,\overset{\star }{\mathop{\text{C}}}\,{{\text{H}}_{2}}=\text{O}\quad \text{O}=\text{CH}-\overset{\star }{\mathop{\text{C}}}\,{{\text{H}}_{2}}\text{Br}\)
GENERAL ORGANIC CHEMISTRY

231678 Arrange the following in increasing order of stability on the basis of reasonance.
(i) \(\mathrm{CH}_2=\mathrm{CH}-\mathrm{CH}=\mathrm{CH}-\stackrel{+}{\mathrm{H}}_2\)
(ii) \(\mathrm{CH}_2=\mathrm{CH}-\stackrel{+}{\mathrm{CH}}-\mathrm{CH}=\mathrm{CH}_2\)
(iii) \(\mathrm{CH}_2=\mathrm{CH}-\stackrel{+}{\mathrm{CH}}-\stackrel{-}{\mathrm{C}}-\stackrel{+}{\mathrm{C}}_2\)
(iv) \(\stackrel{+}{\mathrm{CH}}_2-\mathrm{CH}=\mathrm{CH}-\stackrel{-}{\mathrm{CH}}-\stackrel{+}{\mathrm{CH}}_2\)

1 (ii) $>$ (i) $>$ (iii) $>$ (iv)
2 (iii) $>$ (ii) $>$ (i) $>$ (iv)
3 (i) $>$ (iii) $>$ (ii) $>$ (iv)
4 (iv) $>$ (ii) $>$ (iii) $>$ (i)