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Ch. 19 - Nucleophilic Acyl Substitution 2: Carboxylic Acid Derivatives
Mullins - Organic Chemistry: A Learner Centered Approach 1st Edition
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Capitolo 18, Problema 59a

Predict the product of the following reaction sequences.
(a) Reaction sequence showing a brominated compound with reagents NaCN, LiAlH4, and H3O+ for product prediction.

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Identify the starting material as a brominated alkane with a phenyl group attached, specifically (R)-1-phenylethyl bromide.
In the first step, sodium cyanide (NaCN) in tetrahydrofuran (THF) is used. This is a nucleophilic substitution reaction where the cyanide ion (CN-) will replace the bromine atom, forming a nitrile group. The product will be (R)-1-phenylethyl cyanide.
In the second step, lithium aluminum hydride (LiAlH4) in THF is used. LiAlH4 is a strong reducing agent that will reduce the nitrile group to a primary amine. The product will be (R)-1-phenylethylamine.
In the third step, the reaction mixture is quenched with H3O+. This step is typically used to neutralize any remaining reactive species and to protonate the amine, if necessary, to ensure the final product is in its neutral form.
The final product of the reaction sequence is (R)-1-phenylethylamine, which retains the stereochemistry of the starting material due to the nature of the reactions involved.

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