Question

Draw the main organic product of the following reaction. See the hint below for the strucutres...

Draw the main organic product of the following reaction. See the hint below for the strucutres of the listed reagents and solvent. Omit byproducts.

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Concepts and reason

• Oxidation is the process of adding oxygens to a compound. Alcohols undergo oxidation reaction to give carbonyl compounds.

• Alcohols oxidized using DMSO (dimethyl sulfoxide), oxalyl chloride and organic base (triethyl amine) gives carbonyl compounds.

The selectivity of alcohols plays a major role in Swern oxidation in which primary alcohols gives aldehydes and secondary alcohols gives ketones. Tertiary alcohols are not reactive.

Fundamentals

Swern oxidation: The Swern oxidation is a type of organic reaction in which primary alcohols are oxidized to give aldehydes. The mechanism involves the reaction of dimethyl sulfoxide (DMSO) with oxalyl chloride (COCl)2{\left( {{\rm{COCl}}} \right)_2} followed by the reaction with chloride ion which gives chlorosulfonium salt. The alcohol attacks the chlorosulfonium salt with release of chloride ion which gives alkoxylsulfonium cation followed by proton abstraction which gives carbonyl compounds.

The scheme of the reaction is given below:

OH
1. oxalyl chloride
DMSO
R
CR,
2.TEA
Ri
R2
Reagents:
what
OM
H3C
CH3
Et
Et
Et
Triethylamine
DMSO
Oxalyl chloride

CI
:0
:
He
OQ
s®
H3c
CH3
1
H₃C
CH3
Đ
- H₂CCHE
çi
+
CO(g)
+ CO2(g)
Học
CCH3
H3C
CH3
Chlorosulfonium salt

The mechanism of the reaction is given below:

H3C
CH3
-
:OH
dose-dot
HỌC
CH,
Chlorosulfonium salt
H3C
Ф
сня
HzC
CH3
:OH
Cecot
-HCI
H3C
4
CH3
: OH
Cola
: OH
_
S
+
HC
CH₂

Ans:

The main organic product of the following reaction is given below:

1. oxalyl chloride
DMSO
2.TEA

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