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Choose the Best Answer · Q6

Q.Predict the product Z in the following series of reactions: Ethanoic acid, treated with PCl5, gives X; X, treated with C6H6/anhydrous AlCl3, gives Y; Y, treated with

(i) CH3MgBr then
(ii) H3O+, gives Z. a) (CH3)2C(OH)C6H5 b) CH3CH(OH)C6H5 c) CH3CH(OH)CH2CH3 d) the benzylic alcohol C6H5-CH2-OH (a benzene ring bearing a -CH2OH group)
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Step 1. Ethanoic acid + PCl5 gives X = acetyl chloride (CH3COCl) + POCl3 + HCl (Section 12.12.B.1/12.14.2.1).

Step 2. X (acetyl chloride) + benzene/anhydrous AlCl3 gives Y = acetophenone (CH3-CO-C6H5) via Friedel-Crafts acylation (Section 12.3.D.2).

Step 3. Y (a KETONE) + CH3MgBr (i) then H3O+ (ii) undergoes nucleophilic addition of the Grignard's methyl carbanion to the ketone's carbonyl carbon, giving, after acidic work-up, a TERTIARY alcohol -- since a ketone + RMgX always gives a tertiary alcohol (Section 1 …

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