Why Is This Sequence,CH₂=CHCH₂OH + HBr,then CrO₃/H₂SO₄/H₂O,finally Excess NH₃,not a Good

question 90

Multiple Choice

Why is this sequence,CH₂=CHCH₂OH + HBr,then CrO₃/H₂SO₄/H₂O,finally excess NH₃,not a good method for the preparation of l-alanine?

• A)NH₃ is not sufficiently nucleophilic to perform the final step.
• B)HBr does not add to substituted alkenes.
• C)1° alcohols are not oxidized by CrO₃ in acidic solution.
• D)Initial HBr addition produces a racemic intermediate which leads to racemic product.
• E)Steric hindrance precludes nucleophilic substitution at a 2° carbon atom.

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