The compound shown is treated with DIBAL-H (1 equivalent) in toluene at -78 degC, followed by H3O+. Which structure is the organic product?

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The compound shown is treated with $DIBAL - H$ (1 equivalent) in toluene at $- 7 8^{\circ} C$ , followed by $H X_{3} O X^{+}$ . Which structure is the organic product?

AStructure A
BStructure B
CStructure C
DStructure D

Answer: B

The compound is 4-methylbenzonitrile. One equivalent of the bulky

DIBAL - H

at low temperature adds a single hydride to give an imine-aluminium complex, which stops there. Aqueous acid hydrolyses the imine to 4-methylbenzaldehyde, whereas

LiAlH X_{4}

would have given the amine.

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The compound shown is treated with DIBAL−H (1 equivalent) in toluene at −78∘C, followed by HX3​OX+. Which structure is the organic product?

Answer: B

More questions on Hydride reductions of drawn compounds (LiAlH4 / NaBH4 / DIBAL-H)

The compound shown is treated with $DIBAL - H$ (1 equivalent) in toluene at $- 7 8^{\circ} C$ , followed by $H X_{3} O X^{+}$ . Which structure is the organic product?