Predict the products of the following reaction:
$C H_{3} - C H_{2} - C H_{2} - O - C H_{3} + H B r \to$

Bromopropane and methanol

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Bromomethane and propanol

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Ethanol and bromoethane

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None

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Solution

The correct option is B Bromomethane and propanol
Alkyl ethers are cleaved by the strong acids HI or HBr in a nucleophilic substitution reaction similar to that of alcohols. Protonation of the ethereal oxygen creates a good leaving group, a neutral alcohol molecule. The halide ion, bromide or iodide are both good nucleophiles. Here the reaction follows $S_{N} 2$ type since here no carbocation intermediate is formed.

The reaction is as follows:
$C H_{3} C H_{2} C H_{2} O C H_{3} + H B r 373 K - -- \to C H_{3} C H_{2} C H_{2} O H + C H_{3} B r$

Hence, the correct answer is option (b).

Suggest Corrections

Similar questions

Predict the products of the following reactions:

(i)

(ii)

(iii)

(iv)

C H_{3} - C H = C H_{2} + H B r \to

C H_{3} - C H_{2} - B r + A g C N ⟶ (a q . a l c o h o l)

C H_{3} - C H_{2} - B r + K N O_{2} ⟶ (a q . a l c o h o l)

C H_{3} - I + M g d r y e t h e r - ---- \to

R_{1}

R_{2}

C H_{3} - C H_{2} - C l R_{1} - \to A R_{2} - \to C H_{3} - C H_{3}

i) C H_{3} - C H_{2} - C H_{3} | C H - C H_{2} - O = C H_{2} - C H_{3}

i i) C H_{3} - C H_{2} - C H_{2} - O - C H_{3} | C | C H_{3} - C H_{3}

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