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Preparation of Alcohols from Alkenes

Dehydrobromin...

Question

Dehydrobromination of compounds (A) and (B) yield the same alkene (C). Alkene (C) can
regenerate (A) and (B) by the addition of HBr in the presence and absence of peroxide
respectively. Hydrolysis of (A) and (B) give isomeric products, (D) and (E) respectively.
1, 1?diphenyl ethane is obtained on reaction of (C) with benzene in the presence of H+
.
Give structures of (A) to (E) with reasons.

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Solution

Dear Student,
The products are as follows
(A) and (B) both generate an alkene when heated to lose HBr.
(C) is an alkene which gives a product 1,1-diphenyl ethane hence Phenyl group is already attached to the alkene.
(D) and (E) are alcoholic isomers it indicates that they have same formula but different structure with respect to OH group placement.

Because Ethane is the parent chain the products must have ethane in it.
(A) C₆H₅CH(Br)CH₃(B)C₆H₅CH₂CH₂Br
(C) C₆H₅CH=CH₂
(D) C₆H₅CH(OH)CH₃ (E) C₆H₅CH₂CH₂OH

Regards.

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