
- A
- B
- C
- D
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Correct answer: NONE OF THE GIVEN OPTIONS IS CORRECT; THE MAJOR PRODUCT SHOULD BE $CH_3CD(CL)CHD_2(I)$, WITH $CL$ ON THE MORE SUBSTITUTED CARBON AND $I$ ON THE LESS SUBSTITUTED CARBON.
- Identify the reaction type
The options indicate addition of and across a deuterated alkene. This corresponds to addition of iodine monochloride, , to an alkene.
In , chlorine is more electronegative, so the bond is polarized as:
Thus, the electrophile is effectively .
- Determine the alkene from the products
All options have the carbon skeleton:
with two deuteriums distributed over the double-bond carbons. So the alkene must be:
Now we add across this double bond.
- Mechanism of addition of to alkene
Addition proceeds through formation of an iodonium ion first, because attacks the double bond.
Then opens the halonium ion.
For such additions, the orientation is governed by the carbocation-like character in the bridged intermediate: the nucleophile attacks the more substituted carbon.
So effectively:
- goes first to the alkene,
- finally ends up on the more substituted carbon.
In the alkene
- Left alkene carbon () is more substituted.
- Right alkene carbon () is less substituted.
Therefore:
- goes to the left carbon,
- goes to the right carbon.
So the product should be:
which can be written as:
Matching the options, this is Option B? Let us check carefully.
- Check each option carefully
Starting alkene:
After addition, each double-bond carbon gains one new substituent:
- Left carbon already has and , so it gets either or and no extra H/D.
- Right carbon already has , so it gets either or .
Thus the valid connectivity after addition must look like one of these two regioisomers:
nor
Now inspect options:
-
A:
Impossible: left carbon has become , which would mean deuterium count changed incorrectly. -
B:
This has one on each carbon after addition, so total deuterium count is only 2, whereas alkene had 3 deuteriums. Impossible. -
C:
This puts both and on the same carbon. Not possible for simple addition across a double bond. -
D:
Again only 2 deuteriums total, so impossible.
- Conclusion from chemical reasoning
None of the options exactly matches the chemically correct product expected from addition of to .
The correct major product should be:
or equivalently
Since this is not among the given options, the stored answer C is chemically inconsistent.
- Comparison with stored answer
Stored correct answer: C
But option C is not a valid addition product, since it places both halogens on the same carbon.
Therefore, I disagree with the stored answer.
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