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Question

Which of the following sets of reactions cannot give a carboxylic acid as the final product?

A
RMgX+O=C=Odry ether−−−−(A)H3O+−−(B)
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B
PhCH2CH2CH3i) KMnO4/OH, −−−−−−−−−−−ii) H3O+(A)
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C
CH3(CH2)8CH2OHH2SO4−−−CrO3(A)
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D
RCNi) SnCl2/dil. HCl−−−−−−−−−−(A)ii) H2O/H+−−−−−−(B)
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Solution

The correct option is D RCNi) SnCl2/dil. HCl−−−−−−−−−−(A)ii) H2O/H+−−−−−−(B)
(a)
RMgX+O=C=Odry ether−−−−RO||C(A)OMgXH3O+−−−RO||C(B)OH

(b) This is Stephen's reaction for aldehyde synthesis.
RCNi) SnCl2/dil. HCl−−−−−−−−−−RCH=NH+2Cl(A)ii) H2O/H+−−−−−−RCHO(B)+NH4Cl

(c)
PhCH2CH2CH3i). KMnO4/OH, −−−−−−−−−−−−ii). H3O+PhCOOH(A)

(d) Jones reagent oxidises primary alcohol to the corresponding carboxylic acid.

CH3(CH2)8CH2OHH2SO4, acetone−−−−−−−−CrO3CH3(CH2)8COOH(A)

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