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Question

Aldehydes, Ketones and Carboxylic acids are Carbonyl compounds.
(a) Aldehydes differ from Ketones in their oxidation reactions. Illustrate with one example.
(b) How will you prepare benzaldehyde by Gatterman-Koch reaction?
(c) Write the reactions of carboxylic acid with the following reagents. (Write the chemical equations)
(i) Thionyl chloride (SOCl2)
(ii) Chlorine in presence of small amount of red phosphorous.
(iii) Lithium Aluminium hydride (LiAlH4)/ether.

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Solution

(a) Aldehydes has hydrogen as one of the substituents of carbon. Ketones don't have that hydrogen. The presence of that hydrogen atom makes aldehydes very easy to oxidise.
(b) Refer IMAGE 01
Benzene on reaction with carbon monoxide and HCl in the presence of AlCl3 or CuCl gives Benzaldehyde.
(c)
(i) Carboxylic acid reacts with thionyl chloride which gives acyl chloride and SO2 gas and HCl.
CH3COOH+SOCl2CH3COCl+SO2+HCl
(ii) Chloride presence of small amount of red phosphorous gives αchloro substituted products. This reaction is also called as HVZ (Hell-Volhard-Zelinsky) reaction. Refer IMAGE 02.
(iii) Carboxylic acid on reduction with LiAlH4 gives corresponding Alcohols as LiAlH4 is strong reducing agent. Refer IMAGE 03.

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