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The conversion of propan-1-ol to n-butylamine involves the sequential addition of reagents. The correct sequential order of reagents is

1. (i) SOCl2 (ii) KCN (iii) H2/Ni, Na(Hg)/C2H5OH
2. (i) HCl (ii) H2/Ni, Na(Hg)/C2H5OH
3. (i) SOCl2 (ii) KCN (iii) CH3NH2
4. (i) HCl (ii) CH3NH2

Correct answer: (i) SOCl2 (ii) KCN (iii) H2/Ni, Na(Hg)/C2H5OH

Solution

Propan-1-ol -> (i) SOCl2 gives propyl chloride; (ii) KCN gives butanenitrile (adds one C); (iii) H2/Ni or Na(Hg)/C2H5OH reduces the nitrile to CH3CH2CH2CH2NH2 (n-butylamine). So the order is SOCl2, KCN, then reduction.

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