The structures of the hemiaminal intermediate and the enamine products formed in the given reactions are to be determined. Concept introduction: Aldehydes and ketones contain carbonyl functional group in their parent chain. They are polar molecules due to the presence of an electronegative oxygen atom that tends to attract the electrons in the double bond closer to itself as compared to the carbon atom. The oxygen acquires a partial negative charge and creates a partial positive charge on carbon atom. Aldehydes and ketones easily undergo nucleophilic addition reactions in which the nucleophile attacks at the carbonyl carbon atom. When aldehydes or ketones react with a secondary amine , formation of enamine takes place. The nitrogen analog of an enol is known as enamine. The nucleophilic addition reaction of the secondary amine to the carbonyl carbon atom results in the formation of hemiaminal intermediate which further on dehydration forms the enamine product.

Question

Want to see the full answer?

Answer 1

Question

Chapter 18.11, Problem 17P

Interpretation Introduction

Interpretation:

The structures of the hemiaminal intermediate and the enamine products formed in the given reactions are to be determined.

Concept introduction:

Aldehydes and ketones contain carbonyl functional group in their parent chain. They are polar molecules due to the presence of an electronegative oxygen atom that tends to attract the electrons in the double bond closer to itself as compared to the carbon atom.

The oxygen acquires a partial negative charge and creates a partial positive charge on carbon atom. Aldehydes and ketones easily undergo nucleophilic addition reactions in which the nucleophile attacks at the carbonyl carbon atom.

When aldehydes or ketones react with a secondary amine, formation of enamine takes place. The nitrogen analog of an enol is known as enamine. The nucleophilic addition reaction of the secondary amine to the carbonyl carbon atom results in the formation of hemiaminal intermediate which further on dehydration forms the enamine product.

Expert Solution & Answer

Want to see the full answer?

Check out a sample textbook solution

See solution

Students have asked these similar questions

NMR spectrum of ethyl acetate has signals whose chemical shifts are indicated below. Which hydrogen or set of hydrogens corresponds to the signal at 4.1 ppm? Select the single best answer. The H O HỌC—C—0—CH, CH, 2 A ethyl acetate H NMR: 1.3 ppm, 2.0 ppm, 4.1 ppm Check OA B OC ch B C Save For Later Submit Ass © 2025 McGraw Hill LLC. All Rights Reserved. Terms of Use | Privacy Center |

How many signals do you expect in the H NMR spectrum for this molecule? Br Br Write the answer below. Also, in each of the drawing areas below is a copy of the molecule, with Hs shown. In each copy, one of the H atoms is colored red. Highlight in red all other H atoms that would contribute to the same signal as the H already highlighted red Note for advanced students: In this question, any multiplet is counted as one signal. 1 Number of signals in the 'H NMR spectrum. For the molecule in the top drawing area, highlight in red any other H atoms that will contribute to the same signal as the H atom already highlighted red. If no other H atoms will contribute, check the box at right. Check For the molecule in the bottom drawing area, highlight in red any other H atoms that will contribute to the same signal as the H atom already highlighted red. If no other H atoms will contribute, check the box at right. O ✓ No additional Hs to color in top molecule ง No additional Hs to color in bottom…

in the kinetics experiment, what were the values calculated? Select all that apply.a) equilibrium constantb) pHc) order of reactiond) rate contstant