Sign in
12thPass logo
New chatPYQ LibraryDoubtsRank report
Sign in to see Recents

Your guest activity stays on this device

Sign in to save progress →
Sign in

Hydrocarbons question

2007 · Shift 0 · Q9
Guest · filters and generic practice availableBrowsing as a guest · PYQ filters and generic practice are available. Sign in only for personalised features and saved progress.
  1. PYQ Library
  2. /JEE Main
  3. /Chemistry
  4. /Hydrocarbons
  5. /2007 · Shift 0 · Q9

Hydrocarbons question

2007 · Shift 0 · Q9

JEE MainChemistryHydrocarbonsMCQ+4 / −1
Which of the following reactions will yield 2, 2-dibromopropane?
  1. A
    CH3CH_3CH3​ - CHCHCH = CH2CH_2CH2​ + HBrHBrHBr →\to→
  2. B
    CH3CH_3CH3​ - CCC ≡\equiv≡ CHCHCH + 2HBrHBrHBr →\to→
  3. C
    CH3CHCH_3CHCH3​CH = CHBrCHBrCHBr + HBrHBrHBr →\to→
  4. D
    CH ≡\equiv≡ CH + 2HBr →\to→
View written solutionFree

Correct answer: B

  1. Target product identification

We need to obtain 2,22,22,2-dibromopropane.

Its structure is: CH3−CBr2−CH3CH_3-CBr_2-CH_3CH3​−CBr2​−CH3​ This is a geminal dibromide with both bromine atoms on the middle carbon of propane.


  1. Check each option

Option A

CH3−CH=CH2+HBrCH_3-CH=CH_2 + HBrCH3​−CH=CH2​+HBr This is addition of one mole of HBr to propene.

By Markovnikov addition: CH3−CH=CH2+HBr→CH3−CHBr−CH3CH_3-CH=CH_2 + HBr \rightarrow CH_3-CHBr-CH_3CH3​−CH=CH2​+HBr→CH3​−CHBr−CH3​ Product is 2-bromopropane, not 2,22,22,2-dibromopropane.

So, A is incorrect.


Option B

CH3−C≡CH+2HBrCH_3-C\equiv CH + 2HBrCH3​−C≡CH+2HBr This is propyne reacting with two moles of HBr.

First addition of HBr:

For terminal alkyne, Markovnikov addition gives: CH3−C≡CH+HBr→CH3−C(Br)=CH2CH_3-C\equiv CH + HBr \rightarrow CH_3-C(Br)=CH_2CH3​−C≡CH+HBr→CH3​−C(Br)=CH2​

Second addition of HBr:

Again Markovnikov addition on the alkene gives: CH3−C(Br)=CH2+HBr→CH3−CBr2−CH3CH_3-C(Br)=CH_2 + HBr \rightarrow CH_3-CBr_2-CH_3CH3​−C(Br)=CH2​+HBr→CH3​−CBr2​−CH3​

This is exactly 2,22,22,2-dibromopropane.

So, B is correct.


Option C

CH3CH=CHBr+HBrCH_3CH=CHBr + HBrCH3​CH=CHBr+HBr Here the alkene is already brominated.

Adding HBr across the double bond can give a dibromopropane, but the product would be:

  • bromine already on terminal carbon,
  • incoming bromine adds according to carbocation stability.

The major product is: CH3−CHBr−CH2BrCH_3-CHBr-CH_2BrCH3​−CHBr−CH2​Br which is 1,2-dibromopropane, not 2,22,22,2-dibromopropane.

So, C is incorrect.


Option D

CH≡CH+2HBrCH\equiv CH + 2HBrCH≡CH+2HBr Acetylene with two moles of HBr gives:

First addition: CH≡CH+HBr→CH2=CHBrCH\equiv CH + HBr \rightarrow CH_2=CHBrCH≡CH+HBr→CH2​=CHBr

Second addition: CH2=CHBr+HBr→CH3−CHBr2CH_2=CHBr + HBr \rightarrow CH_3-CHBr_2CH2​=CHBr+HBr→CH3​−CHBr2​

This is 1,11,11,1-dibromoethane, not 2,22,22,2-dibromopropane.

So, D is incorrect.


  1. Conclusion

Only Option B yields 2,22,22,2-dibromopropane.

B\boxed{B}B​


  1. Comparison with stored correct answer

Stored correct answer: B

My derived answer: B

They match.

PreviousNext

More from Hydrocarbons

  • The alkene formed as a major product in the above elimination reaction is Includes diagram2006 · MCQ
  • Reaction of one molecule of HBr with one molecule of 1,3-butadiene at 40oC gives predominantly2005 · MCQ
  • Of the five isomeric hexanes, the isomer which can give two monochlorinated compounds is2005 · MCQ
  • 2 methylbutane on reacting with bromine in the presence of sunlight gives mainly2005 · MCQ
  • Which types of isomerism is shown by 2,3-dichlorobutane?2005 · MCQ
  • Which one of the following has the minimum boiling point?2004 · MCQ
  • On mixing a certain alkane with chlorine and irradiating it with ultravioletlight, it forms only one monochloroalkane. This alkane could be2003 · MCQ
  • Butene-1 may be converted to butane by reaction with2003 · MCQ