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Question

1) - Draw the structures of major monohalo products in each of the following reactions:


2) - Draw the structures of major monohalo products in each of the following reactions:


3) - Draw the structures of major monohalo products in each of the following reactions:


4) - Draw the structures of major monohalo products in each of the following reactions:


5) - Draw the structures of major monohalo products in each of the following reactions:


6) - Draw the structures of major monohalo products in each of the following reactions:


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Solution

1) - Alcohols reacts with thionyl chloride to form alkyl chlorides.
Cyclohexanol will react with thionyl chloride to form chlorocyclohexane with the evolution of sulphur dioxide and hydrogen chloride gas.

This can be shown as -



2) - 1 - Ethyl-4-nitrobenzene undergoes bnzylic bromination in the presence of light or heat.
As benzylic radicals are more stable, so benzylic hydrogen is abstracted.
Hence, the reaction yields 1-(1-Bromoethyl ) -4-nitorbenzene as a product.

This can be given as below:


Mechanism:

3) - Here, hydroxy group is replaced by chloro nucleophile. Formation of intermediate carbocation take place.
The reaction is given below-


Mechanism can be drawn below-


4) - Type of reaction
Markovnikov's reaction: When a protic acid (HX) is added to an asymmetric alkene, the acidic hydrogen attaches itself to the carbon having a greater number of hydrogen substituents whereas the halide group attaches itself to the carbon atom which has a greater number of alkyl substituents.

Here tertiary carbocation is formed as the intermediate.

I gets substituted at carbon containing lesser hydrogen of unsymmetrical alkene.


Mechanism of reaction


5) - Finkelstein Reaction

Finkelstein reaction is a bimolecular nucleophilic substitution reaction (SN 2 reaction) which involves the exchange of halogen atoms.

In Finkelstein reaction, alkyl iodides are prepared by the reaction of alkyl chlorides/bromides with NaI in dry acetone.

Here exchange of nucleophiles takes place.
This can be represented as given below:

CH3CH2Br+NalCH3CH2l+NaBr

6) - It is a type of free radical substitution reaction and involves the following steps:

Initiation
Here bromine free radicals are formed.
This can be drawn below:

Propagation
Here cyclohexene coverts into free radical as given below:


6) - Termination
Here bromine free radical is added on cyclohexene free radical.

This can be drawn as below-


3 - Bromocylohexene is obtained as product.

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