ORGANIC CHEMISTRY (LOOSELEAF)
ORGANIC CHEMISTRY (LOOSELEAF)
6th Edition
ISBN: 9781260475630
Author: SMITH
Publisher: MCG
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Chapter 7, Problem 78P
Interpretation Introduction

(a)

Interpretation: The product of given two-step sequence is to be drawn.

Concept introduction: The replacement or substitution of one functional group with another different functional group in any chemical reaction is termed as substitution reaction. The electron rich chemical species that contains negative charge or lone pair of electrons are known as a nucleophile. In a nucleophilic substitution reaction, nucleophile takes the position of leaving group by attacking the electron deficient carbon atom.

Interpretation Introduction

(b)

Interpretation: The product of given two-step sequence is to be drawn.

Concept introduction: The replacement or substitution of one functional group with another different functional group in any chemical reaction is termed as substitution reaction. The electron rich chemical species that contains negative charge or lone pair of electrons are known as a nucleophile. In a nucleophilic substitution reaction, nucleophile takes the position of leaving group by attacking the electron deficient carbon atom.

Interpretation Introduction

(c)

Interpretation: The product of given two-step sequence is to be drawn.

Concept introduction: The replacement or substitution of one functional group with another different functional group in any chemical reaction is termed as substitution reaction. The electron rich chemical species that contains negative charge or lone pair of electrons are known as a nucleophile. In a nucleophilic substitution reaction, nucleophile takes the position of leaving group by attacking the electron deficient carbon atom.

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Complete the following reaction diagram by giving either the reaction conditions or the missing products. The reaction mechanisms are not required.
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…
2. Draw the structures and explain why CH3CH₂O and CH3CO₂ are good nucleophiles but CH3SO3, water, and alcohols (R-OH) are poor nucleophiles. Propose a 'cutoff' for the amount of negative charge needed to be a good nucleophile. CH3CH₂O CH3CO₂ CH3SO3 H₂O CH₂OH

Chapter 7 Solutions

ORGANIC CHEMISTRY (LOOSELEAF)

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