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Question 67

Consider the following sequence of reactions

image

The major product P is:

tert-butyl alcohol is a tertiary ($$3^\circ$$) alcohol. When heated with copper at $$573\ \text{K}$$, tertiary alcohols cannot undergo dehydrogenation because they do not possess an $$\alpha$$-hydrogen. Instead, they undergo dehydration to form an alkene.

$$\mathrm{(CH_3)_3COH \xrightarrow{Cu/573,K} (CH_3)_2C=CH_2 + H_2O}$$

Thus, the intermediate formed is 2-methylpropene.

In the next step, 2-methylpropene reacts with benzoic acid in the presence of an acid catalyst.

The alkene is first protonated to give the most stable carbocation:

$$\mathrm{(CH_3)_2C=CH_2 + H^+ \rightarrow (CH_3)_3C^+}$$

The oxygen atom of benzoic acid then attacks the tert-butyl carbocation, followed by deprotonation to form an ester:

$$\mathrm{PhCOOH + (CH_3)_3C^+ \rightarrow PhCOOC(CH_3)_3 + H^+}$$

Hence, the final product $$P$$ is tert-butyl benzoate,

$$\mathrm{PhCOOC(CH_3)_3}$$

Therefore, the correct option is (C).

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