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Question 65 of 76

Q.From which of the following one, tertiary butyl alcohol is obtained by the action of methyl magnesium iodide ?

(a) CH3CHOCH_3CHO
(b) CO2CO_2
(c) HCHOHCHO
(d) CH3COCH3CH_3COCH_3
Puducherry TnboardTamil Nadu HSC (DGE) Board 2019MCQ· 1mImportance★★★★★
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CH3MgICH_3MgI adds across the carbonyl of acetone to form an addition product that on hydrolysis gives tertiary butyl alcohol, (CH3)3COH(CH_3)_3COH.

Grignard reagents add to the carbonyl group (>C=O)\big(>C=O\big), and the class of alcohol obtained depends on the carbonyl substrate: formaldehyde (HCHOHCHO) gives a primary alcohol, any other aldehyde gives a secondary alcohol, and a ketone gives a tertiary alcohol. Here CH3MgICH_3MgI attacks acetone: CH3−CO−CH3+CH3MgI→(CH3)3C−OMgI→H3O+(CH3)3C−OHCH_3-CO-CH_3 + CH_3MgI \rightarrow (CH_3)_3C-OMgI \xrightarrow{H_3O^+} (CH_3)_3C-OH (tert-butyl alcohol), because the incoming methyl group joins the two methyls already on the carbonyl carbon to give a carbon bonded to three methyl groups and one −OH-OH. CH3CHOCH_3CHO (option a) would give a secondary a …

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