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Question


C6H5−O||C−CH2I (i)OH−−−−−−→(ii)H30+[P];

C6H5−CH2−CH2−O||C−CH2I (i)NaOHandI2−−−−−−−−−−→(ii)H3O+ [Q]


The products [P] and [Q] formed in the following reactions respectively are :

A
C6H5CHOHCOCH2OH and C6H5CHICOCH3
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B
C6H5CHOHCOCH2OH and C6H5CHICOCH2OH
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C
C6H5CH2CH2COOH and C6H5CH2COCHI2
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D
C6H5CH2CH2COOH and C6H5CH2COOH
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Solution

The correct option is D C6H5CH2CH2COOH and C6H5CH2COOH
For the first reaction, the hydroxide ion deprotonates active methylene group.
This is followed by intramolecular nucleophilic attack and loss of iodide ion to form cyclopropane ring.
Second molecule of hydroxide ion attacks. This is followed by acidification to form product p which is 3-phenyl propanoic acid.
For the second reaction, which is a haloform reaction, two hydrogen atoms of CH2I are replaced with two iodine atoms to form CI3. This is followed by the hydrolysis in alkaline medium to form phenyl acetic acid (product Q) and iodoform.
128315_44836_ans_ab97858d04544003b0523f21844ebcb5.png

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