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NTA Abhyas 2020
Exam
NTA Abhyas
Year
2020
Subject
Chemistry
Chapter
Carboxylic Acid Derivatives

NTA Abhyas 2020 · Chemistry · Carboxylic Acid Derivatives

What represents the best method for converting a carboxylic acid to...

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

Options

  1. AConvert the acid to an acid chloride, and react the acid chloride with water.
  2. BReduce the acid with LiAlH4.LiAl{H}_{4}.
  3. CConvert the acid to an acid chloride, and reduce the acid chloride with lithium aluminium tri(t-butoxy) hydride.
  4. DConvert the acid to an acid chloride, react the acid chloride with a Grignard reagent, and reduce the product with LiAlH4.

Correct answer

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

Step-by-step solution

(i) This method will not work

RCOOH→SOCl2/PCl3/PCl5RCOCl→H2ORCOOHRCOOH\overset{SOC{l}_{2} / PC{l}_{3} / PC{l}_{5}}{→}RCOCl\overset{{H}_{2}O}{→}RCOOH

Aldehyde will not form

(ii) Carboxylic acid are not reduced by LiAlH4.LiAl{H}_{4}.

(iii) This method is best

RCOOH\overset{SOC{l}_{2} / PC{l}_{3} / PC{l}_{5}}{→}RCOCl\overset{lithiumaluminiumtri \left(t -\text{ butoxy }\right)\text{ hydride }.}{→}RCHO \left(aldehyde\right)<br/><br/>(iv)Thismethodwillproducealcoholratherthanaldehyde:<br/><br/><br/><br/> (iv) This method will produce alcohol rather than aldehyde:<br/><br/>RCOOH\overset{SOC{l}_{2} / PC{l}_{3} / PC{l}_{5}}{→}RCOCl\overset{\left(I\right)R^{′}MgBr}{→}RCOR^{′}\overset{LiAl{H}_{4}}{→}{3}^{ο}alcohol
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