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Question

An organic compound A has the molecular formula C7H6O. When A is treated with NaOH followed by acid hydrolysis, it gives two products B and C. When B is oxidized, it gives A, when A and C are each treated separately with PCl5, they give two different products D and E.
(i) Identify A, B, C, D and E.
(ii) Give the chemical reaction when A is treated with NaOH and name the reaction.

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Solution

C7H6O Molecular formula
A Benzaldehyde (C6H5CHO)
(A)2C6H5CHO+NaOH(B)C6H5CH2OHbenzylalcohol+(C)C6H5COOHBenzoicacid
B Benzyl chloride (C6H5CH2OH)
CC6H5COOH (Benzoic acid)
(1) A+PCl5D+E (2) C+PCl5D+E
(i) A Benzaldehyde
B Benzyl alcohol
C Benzoic acid
D Benzoyl chloride
E Phosphoryl chloride
(ii) Cannizzaro Reaction :
2C6H5CHOBenzaldehyde+NaOH C6H5CH2OHBenzylAlcohol+C6H5COONSodiumbenzoate
626468_598242_ans.png

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