If Br2CHCHBr2 is treated with excess of NaCN solution such that all bromides are substituted by nucleophiles, how many different substitution products would be formed in principle which are chiral?Correct answer is '6'. Can you explain this answer?

Question

Answer

Answer

Answer

Explanation:

To understand the number of different chiral substitution products formed when Br2CHCHBr2 is treated with excess NaCN solution, we need to analyze the molecule and the possible substitution reactions.

Molecule Analysis:
Br2CHCHBr2 is a symmetrical molecule with two identical bromine atoms on either side of the central carbon atom. Since the molecule is symmetrical, any substitution reaction that occurs will result in two identical products.

Substitution Reactions:
When Br2CHCHBr2 is treated with excess NaCN solution, the bromide ions (Br-) will be replaced by the nucleophilic cyanide ions (CN-). This substitution reaction is known as nucleophilic substitution.

Possible Substitution Products:
In this case, there are three possible substitution positions on the molecule where the CN- ion can attack and replace the bromide ion. These positions are the two bromine atoms and the carbon atom.

1. Substitution at one Bromine Atom:
If the CN- ion attacks and replaces one of the bromine atoms, two possible products will be formed. However, since the molecule is symmetrical, these two products will be identical and non-chiral. Therefore, we can exclude this possibility.

2. Substitution at both Bromine Atoms:
If the CN- ion attacks and replaces both bromine atoms, two possible products will be formed. However, since the molecule is symmetrical, these two products will be identical and non-chiral. Therefore, we can exclude this possibility as well.

3. Substitution at the Carbon Atom:
If the CN- ion attacks and replaces the carbon atom, two different products can be formed. Since the carbon atom is chiral, the resulting products will also be chiral. However, these two products will be enantiomers of each other.

Total Number of Chiral Products:
Therefore, in total, there are 2 chiral products formed when Br2CHCHBr2 is treated with excess NaCN solution.

Note:
The correct answer provided is '6', which is incorrect based on the analysis. The correct answer should be '2', as explained above.

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