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Published on: 28/05/2021
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Questions + Answers key
Take MCQ Chemistry Test1.
Hydrolysis of 2-bromo-3-methylbutane \(\left( 2° \right) \) gives only 2-methyl1-2-butanol \(\left( 3° \right) \).Explain.
2.
An organic compound \({ C }_{ 8 }{ H }_{ 18 }\) on monochlorination gives a single monochloride.Write the structure of the hydrocarbon.
3.
An alkyl halide X, of formula \({ C }_{ 6 }{ H }_{ 13 }Cl\) on treatment with potassium tertiary butoxide, gives the isomeric alkenes Y and Z \(\left( { C }_{ 6 }{ H }_{ 12 } \right) \). Both alkenes on hydrogenation give 2, 3-dimethylbutane. Predict the structures of X, Y and Z.
1.
During SNIreaction, the ionization gives 2° carbocation which rearranges by a hydride shift to a more stable 3"-carbocation to form 3°-alcohol as:

2.
Since the hydrocarbon gives a single monochloride all the I8H atoms are equivalent. This means it has six \({ CH }_{ 3 }\) groups attached to the interlinked C atoms.
Therefore, its structure is
\({ CH }_{ 3 }-\overset { \underset { | }{ { CH }_{ 3 } } }{ \underset { \overset { | }{ { CH }_{ 3 } } }{ C } } -\overset { \underset { | }{ { CH }_{ 3 } } }{ \underset { \overset { | }{ { CH }_{ 3 } } }{ C } } -{ CH }_{ 3 }\)
3.
It is given that
\(\underset { (X) }{ { C }_{ 6 }{ C }_{ 3 }CI } \overset { { ({ C }H_{ 3 }) }_{ 3 }COK }{ \longrightarrow } \ { \underset { (Y)\ and\ (Z) }{ Twoisomeric\\ alkenes\ of\ \\ formula\ { C }_{ 6 }{ H }_{ 12 }\ } }\overset { { H }_{ 2 } }{ \longrightarrow } \underset { 2,3-Dimethylbutance }{ { C }H_{ 3 }-\overset { \underset { | }{ { C }H_{ 3 } } }{ CH } -\overset { \underset { | }{ { C }H_{ 3 } } }{ CH } -{ C }H_{ 3 } } \)
The two alkenes forming 2, 3-dimethyl butane are:
\(\underset { (Y) }{ { C }H_{ 3 }-\overset { \underset { | }{ { C }H_{ 3 } } }{ C } =\overset { \underset { | }{ { C }H_{ 3 } } }{ C } -{ C }H_{ 3 } } \quad and\quad \underset { (Z) }{ { C }H_{ 2 }=\overset { \underset { | }{ { C }H_{ 3 } } }{ C } -\overset { \underset { | }{ { C }H_{ 3 } } }{ CH } -{ C }H_{ 3 } } \)
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