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Compounds Containing Nitrogen question

2022 · 24 Jun · Shift 2 · Q13
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  5. /2022 · 24 Jun · Shift 2 · Q13

Compounds Containing Nitrogen question

2022 · 24 Jun · Shift 2 · Q13

JEE MainChemistryCompounds Containing NitrogenMCQ+4 / −1
The conversion of propan-1-ol to n-butylamine involves the sequential addition of reagents. The correct sequential order of reagents is
  1. A
    (i) SOCl2SOCl_2SOCl2​ (ii) KCNKCNKCN (iii) H2H_2H2​/NiNiNi, Na(Hg)Na(Hg)Na(Hg)/C2H5OHC_2H_5OHC2​H5​OH
  2. B
    (i) HClHClHCl (ii) H2H_2H2​/NiNiNi, Na(Hg)Na(Hg)Na(Hg)/C2H5OHC_2H_5OHC2​H5​OH
  3. C
    (i) SOCl2SOCl_2SOCl2​ (ii) KCNKCNKCN (iii) CH3NH2CH_3NH_2CH3​NH2​
  4. D
    (i) HClHClHCl (ii) CH3NH2CH_3NH_2CH3​NH2​
View written solutionFree

Correct answer: A

  1. Identify the target transformation

We need to convert propan-1-ol to n-butylamine.

  • Propan-1-ol: CH3CH2CH2OHCH_3CH_2CH_2OHCH3​CH2​CH2​OH
  • n-Butylamine: CH3CH2CH2CH2NH2CH_3CH_2CH_2CH_2NH_2CH3​CH2​CH2​CH2​NH2​

Notice that the product has one extra carbon atom compared to the starting alcohol.


  1. Plan the carbon chain extension

To increase the carbon chain by one carbon, a standard method is:

  • Convert alcohol to alkyl halide
  • React with KCNKCNKCN to form nitrile
  • Reduce nitrile to primary amine

This works because the cyanide carbon becomes part of the chain.


  1. Step 1: Convert propan-1-ol to alkyl halide

Using SOCl2SOCl_2SOCl2​:

CH3CH2CH2OH→SOCl2CH3CH2CH2ClCH_3CH_2CH_2OH \xrightarrow{SOCl_2} CH_3CH_2CH_2ClCH3​CH2​CH2​OHSOCl2​​CH3​CH2​CH2​Cl

So propan-1-ol becomes 1-chloropropane.


  1. Step 2: Chain extension using KCNKCNKCN

Alkyl chloride undergoes nucleophilic substitution with KCNKCNKCN:

CH3CH2CH2Cl→KCNCH3CH2CH2CNCH_3CH_2CH_2Cl \xrightarrow{KCN} CH_3CH_2CH_2CNCH3​CH2​CH2​ClKCN​CH3​CH2​CH2​CN

This gives butanenitrile.

Now the chain has increased from 3 carbons to 4 carbons.


  1. Step 3: Reduce nitrile to primary amine

Reduction of nitrile gives primary amine:

CH3CH2CH2CN→H2/Ni  or  Na(Hg)/C2H5OHCH3CH2CH2CH2NH2CH_3CH_2CH_2CN \xrightarrow{H_2/Ni\;\text{or}\;Na(Hg)/C_2H_5OH} CH_3CH_2CH_2CH_2NH_2CH3​CH2​CH2​CNH2​/NiorNa(Hg)/C2​H5​OH​CH3​CH2​CH2​CH2​NH2​

This is n-butylamine.


  1. Check the options

Option A

(i) SOCl2SOCl_2SOCl2​
(ii) KCNKCNKCN
(iii) H2/NiH_2/NiH2​/Ni, Na(Hg)/C2H5OHNa(Hg)/C_2H_5OHNa(Hg)/C2​H5​OH

This exactly matches the required sequence.

✅ Correct

Option B

(i) HClHClHCl
(ii) H2/NiH_2/NiH2​/Ni, Na(Hg)/C2H5OHNa(Hg)/C_2H_5OHNa(Hg)/C2​H5​OH

This converts alcohol to chloride, but there is no chain extension step using KCNKCNKCN. So it cannot produce n-butylamine.

❌ Incorrect

Option C

(i) SOCl2SOCl_2SOCl2​
(ii) KCNKCNKCN
(iii) CH3NH2CH_3NH_2CH3​NH2​

After forming nitrile, reaction with CH3NH2CH_3NH_2CH3​NH2​ will not give n-butylamine.

❌ Incorrect

Option D

(i) HClHClHCl
(ii) CH3NH2CH_3NH_2CH3​NH2​

No proper carbon chain extension and not a valid route to n-butylamine.

❌ Incorrect


  1. Final answer

The correct sequential order of reagents is:

A\boxed{\text{A}}A​

This agrees with the stored correct answer.

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