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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.

Chemistry
Chemistry
10th Edition
ISBN:9781305957404
Author:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Publisher:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Chapter1: Chemical Foundations
Section: Chapter Questions
Problem 1RQ: Define and explain the differences between the following terms. a. law and theory b. theory and...
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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
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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