- AZero
- BTwo
- CFour
- DSix
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Correct answer: C
- Write the structure of the alkene
3-Methyl-pent-2-ene has the structure:
Numbering:
- C-2 and C-3 are the double-bond carbons.
- A methyl group is attached at C-3.
- Reaction with HBr in presence of peroxide
In the presence of peroxide, HBr adds by the free-radical (anti-Markovnikov) mechanism.
So, in general:
- adds to the less substituted double-bond carbon.
- adds to the more substituted double-bond carbon.
For
goes to C-2 and goes to C-3.
Hence the product is:
This is 2-bromo-3-methylpentane.
- Check for stereocentres
Now examine the product:
-
C-2 is attached to:
These are four different groups, so C-2 is chiral.
-
C-3 is attached to:
These are also four different groups, so C-3 is chiral.
Thus, the product has 2 stereogenic centres.
- Count the possible stereoisomers
Maximum possible stereoisomers for 2 chiral centres:
Now check for meso form.
A meso form is possible only if there is an internal plane of symmetry. Here the molecule is:
The two stereocentres are not symmetrically equivalent because the ends/groups are different, so no meso form exists.
Therefore total stereoisomers .
- Evaluate the options
- A: Zero — incorrect
- B: Two — incorrect
- C: Four — correct
- D: Six — incorrect
Therefore, the correct answer is:
So the correct option is C.
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