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underset("Specific rotation" = +50^(@))(...

`underset("Specific rotation" = +50^(@))(Ph-CH(OH)CH_(3)) overset(SOCl_(2))(rarr) underset(Cl)underset(|)(PhCH) - CH_(3)`
What si the specific rotation of the product?

A

`+50^(@)`

B

`+60^(@)`

C

`-60^(@)`

D

Zero

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AI Generated Solution

The correct Answer is:
To determine the specific rotation of the product formed from the reaction of (Ph-CH(OH)CH₃) with SOCl₂, we can follow these steps: ### Step 1: Understand the Initial Compound The initial compound is (Ph-CH(OH)CH₃), which has a specific rotation of +50°. This indicates that it is dextrorotatory (D). ### Step 2: Identify the Reaction Type The reaction involves the conversion of an alcohol to a halide using thionyl chloride (SOCl₂). This reaction typically proceeds via an SN1 mechanism, which is a unimolecular nucleophilic substitution. ### Step 3: Mechanism of SN1 Reaction In an SN1 reaction, the first step involves the formation of a carbocation intermediate after the leaving group (OH in this case) departs. The stability of the carbocation is crucial, and since we have a phenyl group (Ph) attached, it will stabilize the carbocation. ### Step 4: Retention of Configuration In the SN1 mechanism, there is retention of configuration. This means that if the starting material is dextrorotatory, the product will also be dextrorotatory. However, the specific rotation value will change due to the different substituent (Cl replacing OH). ### Step 5: Determine the New Specific Rotation While the specific rotation will remain positive (since it is still dextrorotatory), it will not retain the same value of +50°. The specific rotation of the product is given as +60°. ### Conclusion Thus, the specific rotation of the product formed from the reaction is +60°. ### Final Answer The specific rotation of the product is +60°. ---

To determine the specific rotation of the product formed from the reaction of (Ph-CH(OH)CH₃) with SOCl₂, we can follow these steps: ### Step 1: Understand the Initial Compound The initial compound is (Ph-CH(OH)CH₃), which has a specific rotation of +50°. This indicates that it is dextrorotatory (D). ### Step 2: Identify the Reaction Type The reaction involves the conversion of an alcohol to a halide using thionyl chloride (SOCl₂). This reaction typically proceeds via an SN1 mechanism, which is a unimolecular nucleophilic substitution. ...
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