Question

In each reaction box, place the best reagent and conditions from the list below. Any help...



In each reaction box, place the best reagent and conditions from the list below. Any help is greatly appreciated!!

Chemistry

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Concepts and reasons

Organic reactions are chemical reactions of organic compounds. Conversion of one organic compound to other is done by suitable reagents.

The given organic reaction is an oxidation reaction in which the reactant gets oxidized through series of steps such as Bromination (Free radical halogenation), hydroxylation (Nucleophilic substitution) and finally oxidation to give the final product. Write the mechanism for each step.

Fundamentals

• Oxidation: It is the process of adding oxygen, removing electron and hydrogens.

• Free radical substitution: In this reaction initially alkane (toluene) is converted to alkyl halide (benzyl halide) using NBS{\rm{NBS}} (N-Bromosuccinimide) as reagent.

• Nucleophilic substitution: In this, Nucleophile (electron rich) forms a bond with an electrophile (electron deficient) and replaces the leaving group.

Mechanism of the reaction:

Step.1: Homolytic cleavage
[
ņ
a
hv
hv
+ Br
-Br
N-Bromosuccinimide
CH2
CH2
Br
+
HBr

Step.2: Reaction of HBr with NBS
N—Br + HBr
N! + Br2
NI Br
H

Step.3 Reaction of Br, with benzyl radical
Br
H2C
BrABr +
+
Br

Br
NaOH
Benzyl alcohol

Mechanism for the oxidation of alcohols using PCC,

--
--
PCC =
CI-CroN
o=ي=0
R-CH2
H
.
Ro + CIN
-Cr
I20
H
OH
R—CH
R
CH,
ال
م
ا
Proton transfer
R-CH2 i
6-Cr
-
.
/ 5
0
}
+
R-
CH

Ans:

The structure of the final product is,

1) NBS, ROOR, hy
2) NaOH
3) PCC

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