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

Haloalkanes and Haloarenes question

2017 · Shift 0 · Q7
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. /Haloalkanes and Haloarenes
  5. /2017 · Shift 0 · Q7

Haloalkanes and Haloarenes question

2017 · Shift 0 · Q7

JEE MainChemistryHaloalkanes and HaloarenesMCQ+4 / −1
3-Methyl-pent-2-ene on reaction with HBr in presence of peroxide forms an addition product. The number of possible stereoisomers for the product is :
  1. A
    Zero
  2. B
    Two
  3. C
    Four
  4. D
    Six
View written solutionFree

Correct answer: C

  1. Write the structure of the alkene

3-Methyl-pent-2-ene has the structure:

CH3−CH=C(CH3)−CH2−CH3\mathrm{CH_3-CH=C(CH_3)-CH_2-CH_3}CH3​−CH=C(CH3​)−CH2​−CH3​

Numbering:

  • C-2 and C-3 are the double-bond carbons.
  • A methyl group is attached at C-3.
  1. Reaction with HBr in presence of peroxide

In the presence of peroxide, HBr adds by the free-radical (anti-Markovnikov) mechanism.

So, in general:

  • Br\mathrm{Br}Br adds to the less substituted double-bond carbon.
  • H\mathrm{H}H adds to the more substituted double-bond carbon.

For

CH3−CH=C(CH3)−CH2−CH3\mathrm{CH_3-CH=C(CH_3)-CH_2-CH_3}CH3​−CH=C(CH3​)−CH2​−CH3​

Br\mathrm{Br}Br goes to C-2 and H\mathrm{H}H goes to C-3.

Hence the product is:

CH3−CH(Br)−CH(CH3)−CH2−CH3\mathrm{CH_3-CH(Br)-CH(CH_3)-CH_2-CH_3}CH3​−CH(Br)−CH(CH3​)−CH2​−CH3​

This is 2-bromo-3-methylpentane.

  1. Check for stereocentres

Now examine the product:

CH3−CH(Br)−CH(CH3)−CH2−CH3\mathrm{CH_3-CH(Br)-CH(CH_3)-CH_2-CH_3}CH3​−CH(Br)−CH(CH3​)−CH2​−CH3​

  • C-2 is attached to:

    • Br\mathrm{Br}Br
    • H\mathrm{H}H
    • CH3\mathrm{CH_3}CH3​
    • CH(CH3)CH2CH3\mathrm{CH(CH_3)CH_2CH_3}CH(CH3​)CH2​CH3​

    These are four different groups, so C-2 is chiral.

  • C-3 is attached to:

    • H\mathrm{H}H
    • CH3\mathrm{CH_3}CH3​
    • CH(Br)CH3\mathrm{CH(Br)CH_3}CH(Br)CH3​
    • CH2CH3\mathrm{CH_2CH_3}CH2​CH3​

    These are also four different groups, so C-3 is chiral.

Thus, the product has 2 stereogenic centres.

  1. Count the possible stereoisomers

Maximum possible stereoisomers for 2 chiral centres:

22=42^2 = 422=4

Now check for meso form.

A meso form is possible only if there is an internal plane of symmetry. Here the molecule is:

CH3−CH(Br)−CH(CH3)−CH2−CH3\mathrm{CH_3-CH(Br)-CH(CH_3)-CH_2-CH_3}CH3​−CH(Br)−CH(CH3​)−CH2​−CH3​

The two stereocentres are not symmetrically equivalent because the ends/groups are different, so no meso form exists.

Therefore total stereoisomers =4=4=4.

  1. Evaluate the options
  • A: Zero — incorrect
  • B: Two — incorrect
  • C: Four — correct
  • D: Six — incorrect

Therefore, the correct answer is:

4\boxed{4}4​

So the correct option is C.

PreviousNext

More from Haloalkanes and Haloarenes

  • The increasing order of the reactivity of the following halides for the SN1 reaction is : Includes diagram2017 · MCQ
  • Which one of the following reagents is not suitable for the elimination reaction ? Includes diagram2016 · MCQ
  • Bromination of cyclohexene under conditions given below yields : Includes diagram2016 · MCQ
  • The synthesis of alkyl fluorides is best accomplished by:2015 · MCQ
  • In SN2​ reactions, the correct order of reactivity for the following compounds: CH3​Cl, CH3​CH2Cl, (CH3​)2​CHCl and (CH3​)3​CCl is:2014 · MCQ
  • The major organic compound formed by the reaction of 1, 1, 1– trichloroethane with silver powder is:2014 · MCQ
  • A solution of (–l) – chloro –1 – phenylethane in toluene racemises slowly in the presence of a small amount of SbCl5​, due to the formation of :2013 · MCQ
  • Compound (A),C8​H9​Br, gives a white precipitate when warmed with alcoholic AgNO3​. Oxidation of (A) gives an acid (B),C8​H6​O4​.(B) easily forms anhydride on…2013 · MCQ