What represents the best method for converting a carboxylic acid to an aldehyde?

Reduce the acid with

L i A l H_{4}

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Convert the acid to an acid chloride, and react the acid chloride with water.

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Convert the acid to an acid chloride, and reduce the acid chloride with lithium aluminium tri(t-butoxy) hydride.

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Convert the acid to an acid chloride, react the acid chloride with a Grignard reagent, and reduce the product with

L i A l H_{4} .

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Solution

The correct option is C Convert the acid to an acid chloride, and reduce the acid chloride with lithium aluminium tri(t-butoxy) hydride.
(i) This method will not work for formation of aldehyde.

$R C O O H S O C l_{2} / P C l_{3} / P C l_{5} - ---------- \to R C O C l H_{2} O - -- \to R C H_{2} O H (a l c o h o l)$

(ii) Carboxylic acids are not reduced by $L i A l H_{4}$

(iii) This method is best to form aldehyde among the given options.

$R C O O H S O C l_{2} / P C l_{3} / P C l_{5} - ---------- \to R C O C l lithium aluminium tri(t-butoxy)hydride - ----------------------- \to R C H O (a l d e h y d e)$

(iv) This method will produce alcohol rather than aldehyde

$R C O O H S O C l_{2} / P C l_{3} / P C l_{5} - ---------- \to R C O C l (I) R M g B r - ----- \to R C O R L i A l H_{4} - --- \to 3^{\circ} a l c o h o l$

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