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Question 61 of 69

Q.Assertion : Hex-4-ennitrile on reaction with Di-isobutyl aluminium hydride followed by Hydrolysis gives Hex-4-enal. Reason : Di-isobutyl aluminium hydride is a selective reducing agent.

(a) Assertion is true but Reason is false.
(b) Both Assertion and Reason are true, but reason is not the correct explanation of assertion.
(c) Both Assertion and Reason are false.
(d) Both Assertion and Reason are true and reason is the correct explanation of assertion.
Tamil Nadu DgeTamil Nadu HSC (DGE) Board 2023MCQ· 1mImportance★★★★★
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DIBAL-H (di-isobutyl aluminium hydride) at low temperature reduces a nitrile only as far as the imine (which hydrolyses in workup to the aldehyde), stopping short of the amine — this is exactly the 'selective reducing agent' behaviour the reason statement describes, and it correctly explains the assertion.

Hex-4-ennitrile (CH3−CH=CH−CH2−CH2−C≡NCH_3-CH=CH-CH_2-CH_2-C\equiv N) treated with DIBAL-H (1 equivalent, usually at low temperature such as −78∘C-78^\circ C) undergoes partial reduction of the nitrile's triple bond to a metalated imine intermediate; this is stable to further reduction under the reaction conditions because DIBAL-H, being bulky (two isobutyl groups) and used in controlled stoichiometry/temperature, does not reduce further. On aqueous acidic hydrolysis (workup), the imine hydrolyses to the corresponding aldehyde, hex-4-enal (CH3−CH=CH−CH2−CH2−CHOCH_3-CH=CH-CH_2-CH_2-CHO) — so the assertion is a true, standard named transformation. The reason — that DIBAL-H is a selective reducing agent — is also true, and is precisely why the reaction stops cle …

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