Textbook Question
Using any necessary reagents, show how you can accomplish the following multistep syntheses.
(c)
629
views
26. Amines
Amines by Reduction
Struggling with Organic Chemistry?
Join thousands of students who trust us to help them ace their exams!Watch the first videoMultiple Choice
Which of the following successfully synthesizes the given target?
A
B
C
D
Verified step by step guidance1
Identify the starting material and the target molecule. The starting material is an alcohol, and the target molecule is an amine.
Consider the first reaction sequence: H2CrO4, H2O, H2SO4. This is a chromic acid oxidation, which typically converts primary alcohols to carboxylic acids. However, our starting material is a secondary alcohol, which would be oxidized to a ketone.
The next step in the first sequence is SOCl2, Et3N. This converts alcohols to alkyl chlorides, but since we have a ketone, this step is not applicable.
The second reaction sequence starts with PBr3, which converts alcohols to alkyl bromides. This is a suitable first step for converting the alcohol to a good leaving group.
The second step in the second sequence is NaCN in THF, which would perform a nucleophilic substitution to replace the bromide with a nitrile group. This is followed by LiAlH4 reduction, which can convert the nitrile to a primary amine, matching the target molecule.
9:12mWatch next
Master The Primary Amines Flowchart with a bite sized video explanation from Johnny
Start learningRelated Videos
Related Practice
Amines by Reduction practice set
Problem sets built by lead tutorsExpert video explanations