Organic Chemistry
Organic Chemistry
11th Edition
ISBN: 9781118133576
Author: T. W. Graham Solomons, Craig Fryhle
Publisher: Wiley, John & Sons, Incorporated
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Chapter 18, Problem 2Q
Interpretation Introduction

Interpretation: The missing reagents and intermediates, in the given synthesis, are to be provided.

Concept introduction:

The compound formed by the reaction of an aldehyde or a ketone with secondary amines, is called an enamine.

Enamines are good nucleophiles that are alkylated, as well as acylated.

The alkylation of enamines goes through SN2 reaction.

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Consider the reaction conditions provided in the question(s) below question. Determine the type of reaction that will occur. Identify the role of potassium tert-butoxide in this reaction. Br KOtBu tBuOH A) strong base B) weak base or nucleophile C) electrophile D) solvent
Alcohols are acidic in nature. Therefore, a strong base can abstract the acidic hydrogen atom of the alcohol in a process known as deprotonation. The alcohol forms an alkoxide ion by losing the proton attached to the oxygen atom of the hydroxyl ( -OH) group. The alkoxide formed can act as a base or a nucleophile depending on the substrate and reaction conditions. However, not all bases can abstract the acidic proton of alcohols and not all alcohols easily lose the proton. Deprotonation depends on the strength of the base and the acidity of the alcohol. Strong bases, such as NaNH2, can easily abstract a proton from almost all alcohols. Likewise, more acidic alcohols lose a proton more easily. Determine which of the following reactions would undergo deprotonation based on the strength of the base and the acidity of the alcohol. Check all that apply. ► View Available Hint(s) CH3CH,OH + NH3 →CH,CH,O-NH CH3 CH3 H3C-C-H+NH3 → H3 C-C-H OH O-NH CH3CH2OH + NaNH, → CH3CH,O-Na* + NH3 CHC12 Cl₂…
Write a synthesis to convert ethane to the following compound shown below. Note: the synthesis has to be conducted in a basic medium throughout. No acidic conditions allowed.

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