ORGANIC CHEM +SG +SAPLING >IP<
ORGANIC CHEM +SG +SAPLING >IP<
6th Edition
ISBN: 9781319171179
Author: LOUDON
Publisher: MAC HIGHER
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Chapter 11, Problem 11.16P
Interpretation Introduction

(a)

Interpretation:

The reason as to why methyl iodide and 1-butanol are formed when methyl ether (1-methoxybutane) is treated with HI and only a little amount of methanol and 1-iodobutane formed is to be stated.

Concept introduction:

Ether cleavage reactions are those reactions in which an ether reacts with HI and HBr to yield less hindered alkyl halide and alcohol. Protonation of oxygen of ether makes alcohol a good leaving group. Primary ether reacts by SN2 mechanism.

Interpretation Introduction

(b)

Interpretation:

The reason as to why 1-iodobutane is formed when reaction mixture in part (a) is heated for a longer time is to be stated.

Concept introduction:

Ether cleavage reactions are those reactions in which an ether reacts with HI and HBr to yield less hindered alkyl halide and alcohol. Protonation of oxygen of ether makes alcohol a good leaving group. Primary ether reacts by SN2 mechanism.

Interpretation Introduction

(c)

Interpretation:

The reason as to why tert-butyliodide and methanol are formed when tert-butyl methyl ether is treated with HI.

Concept introduction:

Ether cleavage reactions are those reactions in which an ether reacts with HI and HBr to yield less hindered alkyl halide and alcohol. Protonation of oxygen of ether makes alcohol a good leaving group. When tertiary ether reacts with alkyl halide the reaction occurs by SN1 mechanism.

Interpretation Introduction

(d)

Interpretation:

The reason as to why tert-butylmethylether cleaves faster than tert-butylmethylsulfide in HBr.

Concept introduction:

Ether cleavage reactions are those reactions in which an ether reacts with HI and HBr to yield less hindered alkyl halide and alcohol. Protonation of oxygen of ether makes alcohol a good leaving group. When tertiary ether reacts with alkyl halide the reaction occurs by SN1 mechanism

Interpretation Introduction

(e)

Interpretation:

The reason as to why enantiomerically pure (S)-2-butanol and methyl bromide are formed when enantiomerically pure (S)-2-methoxybutane is treated with HBr.

Concept introduction:

Ether cleavage reactions are those reactions in which an ether reacts with HI and HBr to yield less hindered alkyl halide and alcohol. Protonation of oxygen of ether makes alcohol a good leaving group. Primary ether reacts by SN2 mechanism.

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Chapter 11 Solutions

ORGANIC CHEM +SG +SAPLING >IP<

Ch. 11 - Prob. 11.11PCh. 11 - Prob. 11.12PCh. 11 - Prob. 11.13PCh. 11 - Prob. 11.14PCh. 11 - Prob. 11.15PCh. 11 - Prob. 11.16PCh. 11 - Prob. 11.17PCh. 11 - Prob. 11.18PCh. 11 - Prob. 11.19PCh. 11 - Prob. 11.20PCh. 11 - Prob. 11.21PCh. 11 - Prob. 11.22PCh. 11 - Prob. 11.23PCh. 11 - Prob. 11.24PCh. 11 - Prob. 11.25PCh. 11 - Prob. 11.26PCh. 11 - Prob. 11.27PCh. 11 - Prob. 11.28PCh. 11 - Prob. 11.29PCh. 11 - Prob. 11.30PCh. 11 - Prob. 11.31PCh. 11 - Prob. 11.32PCh. 11 - Prob. 11.33PCh. 11 - Prob. 11.34PCh. 11 - Prob. 11.35PCh. 11 - Prob. 11.36PCh. 11 - Prob. 11.37PCh. 11 - Prob. 11.38PCh. 11 - Prob. 11.39PCh. 11 - Prob. 11.40PCh. 11 - Prob. 11.41PCh. 11 - Prob. 11.42PCh. 11 - Prob. 11.43PCh. 11 - Prob. 11.44APCh. 11 - Prob. 11.45APCh. 11 - Prob. 11.46APCh. 11 - Prob. 11.47APCh. 11 - Prob. 11.48APCh. 11 - Prob. 11.49APCh. 11 - Prob. 11.50APCh. 11 - Prob. 11.51APCh. 11 - Prob. 11.52APCh. 11 - Prob. 11.53APCh. 11 - Prob. 11.54APCh. 11 - Prob. 11.55APCh. 11 - Prob. 11.56APCh. 11 - Prob. 11.57APCh. 11 - Prob. 11.58APCh. 11 - Prob. 11.59APCh. 11 - Prob. 11.60APCh. 11 - Prob. 11.61APCh. 11 - Prob. 11.62APCh. 11 - Prob. 11.63APCh. 11 - Prob. 11.64APCh. 11 - Prob. 11.65APCh. 11 - Prob. 11.66APCh. 11 - Prob. 11.67APCh. 11 - Prob. 11.68APCh. 11 - Prob. 11.69APCh. 11 - Prob. 11.70APCh. 11 - Prob. 11.71APCh. 11 - Prob. 11.72APCh. 11 - Prob. 11.73APCh. 11 - Prob. 11.74APCh. 11 - Prob. 11.75APCh. 11 - Prob. 11.76APCh. 11 - Prob. 11.77APCh. 11 - Prob. 11.78APCh. 11 - Prob. 11.79APCh. 11 - Prob. 11.80APCh. 11 - Prob. 11.81AP
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