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Basics of Organic Chemistry question

2007 · Shift 2 · Q7
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Basics of Organic Chemistry question

2007 · Shift 2 · Q7

JEE AdvancedChemistryBasics of Organic ChemistryMCQ+3 / −1
The number of stereoisomers obtained by bromination of transtranstrans-2-butene is :
  1. A
    1
  2. B
    2
  3. C
    3
  4. D
    4
View written solutionFree

Correct answer: A

Step-by-step solution:

  1. Identify the Reactants and Reaction:

    • The reactant is transtranstrans-2-butene, an alkene with the chemical formula CH3CH=CHCH3CH_3CH=CHCH_3CH3​CH=CHCH3​. The trans configuration means the two methyl (CH3CH_3CH3​) groups are on opposite sides of the double bond.
    • The reaction is bromination, which is the addition of a bromine molecule (Br2Br_2Br2​) across the double bond.
  2. Determine the Reaction Mechanism and Stereochemistry:

    • The addition of halogens like Br2Br_2Br2​ to an alkene is an electrophilic addition reaction.
    • The mechanism involves the formation of a cyclic bromonium ion intermediate. The subsequent attack by the bromide ion (Br−Br^−Br−) occurs from the side opposite to the cyclic intermediate. This is known as anti-addition.
  3. Analyze the Stereochemical Outcome:

    • We are starting with a trans alkene and performing an anti addition. There is a general rule for the stereochemical outcome of such reactions on symmetrical alkenes:
      • cis + syn addition → meso
      • cis + anti addition → racemic (pair of enantiomers)
      • trans + syn addition → racemic (pair of enantiomers)
      • trans + anti addition → meso
    • Following this rule, the bromination of transtranstrans-2-butene (a trans alkene) via anti addition should yield a meso compound.
  4. Illustrate the Reaction Product:

    • The product of the reaction is 2,3-dibromobutane (CH3−CH(Br)−CH(Br)−CH3CH_3-CH(Br)-CH(Br)-CH_3CH3​−CH(Br)−CH(Br)−CH3​). This molecule has two chiral centers at carbon-2 and carbon-3.

    • Let's visualize the reaction using Fischer projections to confirm the formation of a meso compound.

    • First, draw the structure of transtranstrans-2-butene in a way that is suitable for showing the addition. The main carbon chain is vertical. CH3∣H−C∣∣C−H∣CH3 \begin{array}{c} CH_3 \\ | \\ H-C \\ || \\ C-H \\ | \\ CH_3 \end{array}CH3​∣H−C∣∣C−H∣CH3​​

    • In an anti-addition, the two bromine atoms add from opposite faces of the double bond. In a Fischer projection, this means they will appear on opposite sides (one on the left, one on the right). CH3∣Br−C−H−−−∣−−−H−C−Br∣CH3 \begin{array}{c} CH_3 \\ | \\ Br - C - H \\ ---|--- \\ H - C - Br \\ | \\ CH_3 \end{array}CH3​∣Br−C−H−−−∣−−−H−C−Br∣CH3​​

  5. Identify the Product as a Meso Compound:

    • The resulting structure is a Fischer projection of 2,3-dibromobutane.
    • Let's analyze this structure for elements of symmetry. A meso compound is an achiral compound that has chiral centers. It is achiral because it possesses an internal plane of symmetry or a center of inversion in one of its conformations.
    • The Fischer projection shown for the product has a center of inversion. If you trace a line from any group through the midpoint of the C2-C3 bond, you find an identical group at an equal distance on the other side. For example, the top CH3CH_3CH3​ and bottom CH3CH_3CH3​, the left BrBrBr and right BrBrBr, the right HHH and left HHH.
    • A molecule with a center of inversion is achiral. This specific stereoisomer is called meso-2,3-dibromobutane.
    • Alternatively, we can assign the R/S configuration to the chiral centers. The top chiral center (C2) is (S), and the bottom chiral center (C3) is (R). The molecule is (2S, 3R)-2,3-dibromobutane. Its mirror image would be (2R, 3S)-2,3-dibromobutane. For a symmetrical molecule like this, the (2S, 3R) and (2R, 3S) forms are identical and represent the same single meso compound.
  6. Conclusion:

    • The bromination of transtranstrans-2-butene proceeds via anti-addition to form a single product, the meso-2,3-dibromobutane.
    • A meso compound is a single stereoisomer.
    • Therefore, the number of stereoisomers obtained is 1.

Final Answer Check:

  • The question asks for the number of stereoisomers obtained.
  • Our analysis shows that only one product, a meso compound, is formed.
  • The number of stereoisomers is 1.
  • This corresponds to option A.
Previous

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