The reaction of cyclohexanone (1) and N,N-dimethylamine (2) with (i) sodium triacetoxyborohydride (NABH(OAc)3) in methanol with acetic acid (ACOH) affords N,N- dimethylcyclohexanamine (3) in high yield. However, if anhydrous HCI is used (ii), the reaction yield of (3) is low and a side reaction occurs to produce alcohol (4). i. NaBH(OAc)3 ii. NaBH(OAc)3 OH Acetic acid, methanol HCI, Methanol 95% yield Low yield 2 3 4.
The reaction of cyclohexanone (1) and N,N-dimethylamine (2) with (i) sodium triacetoxyborohydride (NABH(OAc)3) in methanol with acetic acid (ACOH) affords N,N- dimethylcyclohexanamine (3) in high yield. However, if anhydrous HCI is used (ii), the reaction yield of (3) is low and a side reaction occurs to produce alcohol (4). i. NaBH(OAc)3 ii. NaBH(OAc)3 OH Acetic acid, methanol HCI, Methanol 95% yield Low yield 2 3 4.
Organic Chemistry
8th Edition
ISBN:9781305580350
Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Publisher:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Chapter16: Aldehydes And Ketones
Section: Chapter Questions
Problem 16.47P: The base-promoted rearrangement of an -haloketone to a carboxylic acid, known as the Favorskii...
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Draw a reaction mechanism for the reductive animation sequence. Highlight tautomers present in reaction
![The reaction of cyclohexanone (1) and N,N-dimethylamine (2) with (i) sodium
triacetoxyborohydride (NABH(OAc)3) in methanol with acetic acid (ACOH) affords N,N-
dimethylcyclohexanamine (3) in high yield. However, if anhydrous HCI is used (ii), the
reaction yield of (3) is low and a side reaction occurs to produce alcohol (4).
ii. NaBH(OAc)3
HCI, Methanol
i. NABH(OAc)3
N.
OH
Acetic acid, methanol
+.
95% yield
Low yield
2
3
4](/v2/_next/image?url=https%3A%2F%2Fcontent.bartleby.com%2Fqna-images%2Fquestion%2Ffd303584-3b35-48e8-acc9-a84c883729fd%2F933e889a-6ab3-4b0a-b600-64fdbcc8e3ae%2Fh3rl5e8_processed.jpeg&w=3840&q=75)
Transcribed Image Text:The reaction of cyclohexanone (1) and N,N-dimethylamine (2) with (i) sodium
triacetoxyborohydride (NABH(OAc)3) in methanol with acetic acid (ACOH) affords N,N-
dimethylcyclohexanamine (3) in high yield. However, if anhydrous HCI is used (ii), the
reaction yield of (3) is low and a side reaction occurs to produce alcohol (4).
ii. NaBH(OAc)3
HCI, Methanol
i. NABH(OAc)3
N.
OH
Acetic acid, methanol
+.
95% yield
Low yield
2
3
4
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