1.2.HO H1.Br2.+ SOCI₂a = Proton transferb = Lewis acid/baseC = Radical chain substitutiond Radical chain additionP(n-Bu)3P(n-Bu)4e =f = E1 Eliminationg = E2 EliminationElectrophilic additionH CIBr+SO₂ + HCIIdentify the mechanism by which each of the reactions above proceeds from among the mechanisms listed. Use theletters a j for your answers.h = SN1 Nucleophilic substitutioni = SN2 Nucleophilic substitutionj = Electrophilic aromatic substitution

Answered: 1. 2. HO H 1. 'Br 2. SOCI₂ a = Proton…

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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Question

1.
2.
HO H
1.
Br
2.
+ SOCI₂
a = Proton transfer
b = Lewis acid/base
C = Radical chain substitution
d Radical chain addition
P(n-Bu)3
P(n-Bu)4
e =
f = E1 Elimination
g = E2 Elimination
Electrophilic addition
H CI
Br
+
SO₂ + HCI
Identify the mechanism by which each of the reactions above proceeds from among the mechanisms listed. Use the
letters a j for your answers.
h = SN1 Nucleophilic substitution
i = SN2 Nucleophilic substitution
j = Electrophilic aromatic substitution

Expert Solution

Step 1

Reaction of an alcohol with thionyl chloride:

The lone pair in oxygen atom of the alcohol attacks sulphur center to displace a chloride ion from thionyl chloride and forms a protonated alkyl chlorosulfite intermediate. Following that, the free chloride ion attacks at the carbon center attached to the alcoholic oxygen atom and giving rise to the alkyl halide as shown in the mechanism. The reaction goes through a nucleophilic substitution SN2 reaction.

Similarly, the lone pair of phosphorus atoms in P(n-Bu)3 attacks at the carbon atom attached to the bromine atom as this carbon center is most electrophilic and thereby, forming +P(n-Bu)4 Br- as product. This reaction is also go through the nucleophilic substitution SN2 reaction.

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