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Question

Identify product D in the following reaction sequence.
CH3CH3|C|CH3 CH2CH2OHK2Cr2O7;H2SO4H2O,heatASOCl2B(CH3)2NH2moleC1.LiAlH4diethylether2.H2OD

A
CH3CH3|C|CH3CH2CN
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B
CH3CH3|C|CH3CH2CH2N(CH3)2
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C
CH3CH3|C|CH3CH2N(CH3)2|CHN(CH3)2
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D
CH3CH3|C|CH3CH2C|OHHN(CH3)2
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Solution

The correct option is B CH3CH3|C|CH3CH2CH2N(CH3)2
(CH3)3CCH2CH2OHK2Cr2O7,H2SO4−−−−−−−−−H2O,heat(CH3)3CCH2O||COH(A)
Oxidation of alcohol with K2Cr2O7 to carboxylic acids
(CH3)3CCH2O||COHSOCl2−−−(CH3)3CCH2O||CCl(B)
Carboxilic acid upto treatment with SOCl2, acid chloride forms
(CH3)3CCH2O||CCl(CH3)2NH−−−−−−2mole(CH3)3CCH2O||CN|CH3CH3(C)
Acid chloride on reaction with 2o amide forms 2o amine
(CH3)3CCH2O||CN(CH3)21.LiAIH4,−−−−−−diethylether2.H2OCH3CH3|C|CH3CH2CH2N|CH3CH3(D)

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