Which of the organic products of the following reactions has the least boiling point?

{C H}_{3} - {C H}_{2} - C O O H L i A l H_{4} - --- \to H_{2} O

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{C H}_{3} - C ∥ O - {C H}_{3} L i B H_{4} - --- \to H_{2} O

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{C H}_{3} - {C H}_{2} - C H O L i B H_{4} - --- \to H_{2} O

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{C H}_{3} - C H = {C H}_{2} {({B H}_{3})}_{2} - ------ \to H_{2} O_{2}, {O H}^{-}

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Solution

The correct option is B ${C H}_{3} - C ∥ O - {C H}_{3} L i B H_{4} - --- \to H_{2} O$
In option A, the product formed is the primary alcohol because $L i A l H_{4}$ reduces the carbonyl bond only.

${C H}_{3} - C H_{2} - C ∥ O - O H L i A l H_{4} - --- \to H_{2} O C H_{3} - C H_{2} - C H_{2} O H 1^{o} a l c o h o l$

The organic product of the reaction of option (B) has the least boiling point.
In reaction of option (B), a secondary alcohol is obtained. In all the remaining reactions, a primary alcohol is obtained.
The boiling point of alcohol decreases with increase in branching. Thus, $2 -$ propanal has lower boiling point than $1 -$ propanal.
${C H}_{3} - C ∥ O - {C H}_{3} L i B H_{4} - --- \to H_{2} O {C H}_{3} - C | O H H - {C H}_{3}$

(C) ${C H}_{3} - {C H}_{2} - C H O L i B H_{4} - --- \to H_{2} O C H_{3} - C H_{2} - C H_{2} O H 1^{o} a l c o h o l$

In option D, the product formed is the primary alcohol because hydroboration of terminal alkene forms primary alkene the carbonyl bond only.

${C H}_{3} - C H = {C H}_{2} {({B H}_{3})}_{2} - ------ \to H_{2} O_{2}, {O H}^{-} C H_{3} - C H_{2} - C H_{2} O H 1^{o} a l c o h o l$

Boiling point order of alcohols are-
Primary > secondary > Tertiary alcohols

Option B is correct

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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}

S_{N} 2

c o n c . H C l :

(a) C H_{3} - C H_{2} - O H A n h y Z n C l_{2} / △ - -------- \to C H_{3} - C H_{2} - C l

(b) C H_{3} - C H_{3} | C | C H_{3} - C H_{2} O H A n h y Z n C l_{2} / △ - -------- \to C H_{3} - C H_{1} | C | C H_{3} - C H_{2} - C H_{3}

(c) C H_{3} - O H | C | C H_{3} - C H_{3} A n h y Z n C l_{2} / △ - -------- \to C H_{3} - C l | C | C H_{3} - C H_{3}

(d) C H_{2} = C H - C H_{2} - O H A n h y Z n C l_{2} / △ - -------- \to C H_{2} = C H - C H_{2} - C l

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