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Compounds Containing Nitrogen question

2023 · 13 Apr · Shift 2 · Q11
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Compounds Containing Nitrogen question

2023 · 13 Apr · Shift 2 · Q11

JEE MainChemistryCompounds Containing NitrogenMCQ+4 / −1

Match List I with List II

1 - Bromopropane is reacted with reagents in List I to give product in List II

LIST I - Reagent LIST II - Product
A. KOH\mathrm{KOH}KOH (alc) I. Nitrile
B. KCN\mathrm{KCN}KCN (alc) II. Ester
C. AgNO2\mathrm{AgNO_2}AgNO2​ III. Alkene
D. H3CCOOAg\mathrm{H_3CCOOAg}H3​CCOOAg IV. Nitroalkane

Choose the correct answer from the options given below:

  1. A
    A-I, B-II, C-III, D-IV
  2. B
    A-IV, B-III, C-II, D-I
  3. C
    A-III, B-I, C-IV, D-II
  4. D
    A-I, B-III, C-IV, D-II
View written solutionFree

Correct answer: C

  1. Identify the substrate

The given substrate is 1-bromopropane, i.e.

CH3CH2CH2Br\mathrm{CH_3CH_2CH_2Br}CH3​CH2​CH2​Br

We match each reagent with the product formed.

  1. Reaction with KOH\mathrm{KOH}KOH (alc)

Alcoholic KOH promotes dehydrohalogenation (elimination of HBr), giving an alkene.

CH3CH2CH2Br→alcKOHCH3CH=CH2\mathrm{CH_3CH_2CH_2Br \xrightarrow[alc]{KOH} CH_3CH=CH_2}CH3​CH2​CH2​BrKOHalc​CH3​CH=CH2​

So,

  • A →\to→ III (Alkene)
  1. Reaction with KCN\mathrm{KCN}KCN (alc)

KCN\mathrm{KCN}KCN gives nucleophilic substitution via carbon end of cyanide ion, forming a nitrile.

CH3CH2CH2Br+KCN→CH3CH2CH2CN\mathrm{CH_3CH_2CH_2Br + KCN \rightarrow CH_3CH_2CH_2CN}CH3​CH2​CH2​Br+KCN→CH3​CH2​CH2​CN

So,

  • B →\to→ I (Nitrile)
  1. Reaction with AgNO2\mathrm{AgNO_2}AgNO2​

Nitrite ion is ambident, but with AgNO2\mathrm{AgNO_2}AgNO2​, attack occurs through nitrogen, giving a nitroalkane.

CH3CH2CH2Br+AgNO2→CH3CH2CH2NO2\mathrm{CH_3CH_2CH_2Br + AgNO_2 \rightarrow CH_3CH_2CH_2NO_2}CH3​CH2​CH2​Br+AgNO2​→CH3​CH2​CH2​NO2​

So,

  • C →\to→ IV (Nitroalkane)
  1. Reaction with H3CCOOAg\mathrm{H_3CCOOAg}H3​CCOOAg (silver acetate)

Silver acetate gives nucleophilic substitution to form an ester:

CH3CH2CH2Br+CH3COOAg→CH3COOCH2CH2CH3\mathrm{CH_3CH_2CH_2Br + CH_3COOAg \rightarrow CH_3COOCH_2CH_2CH_3}CH3​CH2​CH2​Br+CH3​COOAg→CH3​COOCH2​CH2​CH3​

So,

  • D →\to→ II (Ester)
  1. Final matching

Thus the correct matching is:

A−III,B−I,C−IV,D−IIA-III,\quad B-I,\quad C-IV,\quad D-IIA−III,B−I,C−IV,D−II

This corresponds to Option C.

  1. Comparison with stored answer

Stored correct answer = C

Our derived answer = C

Hence, the derived answer agrees with the stored answer.

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