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Provide the major product expected for the following reactions. Omit byproducts. Ignore stereochemistry. Hint: if more...

Provide the major product expected for the following reactions. Omit byproducts. Ignore stereochemistry. Hint: if more than one product is possible, draw only the one that fits in the context of this two-step scheme.

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Provide the major product expected for the following reactions. Omit byproducts. Ignore stereochemistry. Hint: if more than one product is possible, draw only the one that fits in the context of this two-step scheme.
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Answer #1
Concepts and reason

• Allylic bromination is the replacement of hydrogen atom by bromine atom at allylic position.

• The allylic position is adjacent to carbon position to the double bond. NBS (N-Bromo Succinimide) is used for brominating at allylic positions, in the presence of peroxides, light or heat.

• E2 elimination reaction is a bi-molecular elimination reaction.

• This elimination process is a single-step process, which follows the concerted mechanism.

• In E2 elimination reaction, the intermediate is in a transition state.

Fundamentals

Allylic bromination undergoes through a free radical mechanism by NBS in the presence of peroxides, light or heat.

NBS is catalyzed by the HBr{\rm{HBr}} , which is present in NBS as a small quantity. That is how the direct bromination of double bond is controlled. CCl4{\rm{CC}}{{\rm{l}}_{\rm{4}}} acts as a solvent in this reaction.

This reaction undergoes a radical chain of reactions, which consist of mainly three steps:

I. Initiation

II.Propagation

III.Termination

E2 elimination reaction: The rate of the reaction depends on both, the base and the substrate. Therefore, the E2 elimination reaction is known as the bi-molecular elimination reaction.

rate[substrate][base]{\rm{rate}}\, \propto \,\left[ {{\rm{substrate}}} \right]\left[ {{\rm{base}}} \right]

NBS catalyzed reaction by HBr{\rm{HBr}} is shown below.

N-
Br + HBr
N-
H
+
Br—
Br
NBS

The hemolytic cleavage of bromine molecule is due to the presence of heat.

The initiation step:

Br-
Br
Br +Br

Propagation (1)

+ HBr
Br

Propagation (2)

+
Bi
Br!

Termination

Br
+
Br
-
Br—
Br

The given base is tertiary butoxide, which is a strong base in nature, and follows the E2 elimination reaction path way with the obtained brominated product of the given substrate.

(CH3)2COK
+ HBr
(CH3)3COH

The overall reaction is as follows:

NBS
8==
(CH3)3 COK
(CH3)3COH
hv or
ROOR
Br

Ans:

The overall reaction is as follows:

NBS
8==
(CH3)3 COK
(CH3)3COH
hv or
ROOR
Br

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