We have seen that the alpha carbon atom of an enamine can function as a nucleophile in a Michael reaction, and in fact, enamines can function as nucleophiles in a wide variety of reactions. For example, an enamine will undergo alkylation when treated with an alkyl halide. Draw the structure of intermediate A and the alkylation product B in the following reaction scheme (J. Am. Chem. Soc. 1954, 76, 2029-2030): TSOH -H₂O NH A 1) CHgI 2) H₂O+ B + NH Modify the given copy of the starting material to draw compound A. If needed, use the single bond tool to interconvert between double and single bonds.

We have seen that the alpha carbon atom of an enamine can function as a nucleophile in a Michael reaction, and in fact, enamines can function as nucleophiles in a wide variety of reactions. For example, an enamine will undergo alkylation when treated with an alkyl halide. Draw the structure of intermediate A and the alkylation product B in the following reaction scheme (J. Am. Chem. Soc. 1954, 76, 2029-2030): TSOH -H₂O NH A 1) CHgI 2) H₂O+ B + NH Modify the given copy of the starting material to draw compound A. If needed, use the single bond tool to interconvert between double and single bonds.

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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Concept explainers

Aldehydes and Ketones

Aldehydes and ketones are organic compounds that have a carbonyl group, C = O, as their functional group. They both differ in the placement of this carbonyl group in their structures.

Question

We have seen that the alpha carbon atom of an enamine can function as a nucleophile in a Michael reaction, and in fact,
enamines can function as nucleophiles in a wide variety of reactions. For example, an enamine will undergo alkylation
when treated with an alkyl halide. Draw the structure of intermediate A and the alkylation product B in the following
reaction scheme (J. Am. Chem. Soc. 1954, 76, 2029-2030):
TSOH
-H₂O
NH
A
1) CHgI
2) H₂O+
B +
NH
Modify the given copy of the starting material to draw compound A. If needed, use the single bond tool to interconvert
between double and single bonds.
Edit Drawing

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