Single Choice

In the following reaction sequence: $$\underset{(C_3H_6Cl_2)}{I} \xrightarrow {KOH(aq)} II \xrightarrow[(ii)H_2O/H^+]{(i)CH_3MgBr} III \xrightarrow{Anhy.ZnCl_2+Con.HCl} $$ give trubidity immediately

A$$Cl - \underset{Cl}{\underset{|}{CH}} - CH_2 - CH_3$$
B$$\underset{Cl}{\underset{|}{CH_2}} - CH_2 - \underset{Cl}{\underset{|}{CH_2}}$$
C$$CH_3 - \overset{Cl}{\overset{|}{\underset{CH_3}{\underset{|}{C}}}} - CH_3$$
Correct Answer
D$$\underset{Cl}{\underset{|}{CH_2}} - \underset{Cl}{\underset{|}{CH}} - CH_3$$

Solution

The compound (I) is represented by the option (C).

$$\displaystyle \underset{(C_3H_6Cl_2), \: I}{ CH_3 - \overset{ \displaystyle Cl}{\overset{|}{\underset{ \displaystyle Cl}{\underset{|}{C}}}} - CH_3 } \overset{KOH(aq)}{\rightarrow} \underset {II}{CH_3 - \overset{ \displaystyle OH}{\overset{|}{\underset{ \displaystyle OH}{\underset{|}{C}}}} - CH_3} \rightleftharpoons CH_3 - \underset{ \displaystyle O}{\underset{||}{C}} - CH_3 \\ \:
\xrightarrow[(ii)H_2O/H^+]{(i)CH_3MgBr} \underset {III}{CH_3 - \overset{ \displaystyle OH}{\overset{|}{\underset{ \displaystyle CH_3}{\underset{|}{C}}}} - CH_3 } \overset{Anhy.ZnCl_2+Con.HCl}{\rightarrow} CH_3 - \overset{ \displaystyle Cl}{\overset{|}{\underset{ \displaystyle CH_3}{\underset{|}{C}}}} - CH_3 $$
Hydrolysis of compound (I), a geminal dichloride gives compound (II), a geminal diol. It loses a molecule of water to form acetone. Attack of grignard reagent gives tertiary alcohol.
Tertiary alcohols give rapid turbidity with Lucas reagent $$\displaystyle Anhy. ZnCl_2+Con.HCl$$

Hence, the correct option is C

SIMILAR QUESTIONS

Haloalkanes and Haloarenes

On heating with bleaching powder, ethyl alcohol is converted into:

Haloalkanes and Haloarenes

The best method to prepare neopentyl chloride is:

Haloalkanes and Haloarenes

Write the structure of the major organic product in each of the following reactions: $$CH_3CH_2CH_2OH+SOCl_2 \rightarrow $$

Haloalkanes and Haloarenes

Which of the following reaction(s) can be used for the preparation of alkyl halides? (I) $$CH_3CH_2OH+HCl\xrightarrow {anh.ZnCl_2}$$ (II) $$CH_3CH_2OH+HCl\rightarrow$$ (III) $$(CH_3)_3COH+HCl\rightarrow$$ (IV) $$(CH_3)_2CHOH+HCl\xrightarrow {anh.ZnCl_2}$$

Haloalkanes and Haloarenes

Which statement is correct?

Haloalkanes and Haloarenes

Suggest the reagent that could be used to prepare these alkyl halides from alcohols.

Haloalkanes and Haloarenes

The product $$(B)$$ is:

Haloalkanes and Haloarenes

The number of possible monobromo products is (excluding stereoisomers):

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