- A1
- B2
- C3
- D4
View written solutionFree
Correct answer: A
Step-by-step solution:
-
Identify the Reactants and Reaction:
- The reactant is -2-butene, an alkene with the chemical formula . The trans configuration means the two methyl () groups are on opposite sides of the double bond.
- The reaction is bromination, which is the addition of a bromine molecule () across the double bond.
-
Determine the Reaction Mechanism and Stereochemistry:
- The addition of halogens like 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 () occurs from the side opposite to the cyclic intermediate. This is known as anti-addition.
-
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+synaddition →mesocis+antiaddition →racemic(pair of enantiomers)trans+synaddition →racemic(pair of enantiomers)trans+antiaddition →meso
- Following this rule, the bromination of -2-butene (a trans alkene) via anti addition should yield a meso compound.
- 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:
-
Illustrate the Reaction Product:
-
The product of the reaction is 2,3-dibromobutane (). 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 -2-butene in a way that is suitable for showing the addition. The main carbon chain is vertical.
-
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).
-
-
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 and bottom , the left and right , the right and left .
- 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.
-
Conclusion:
- The bromination of -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.
More from Basics of Organic Chemistry
- Match the reactions in List-I with the features of their products in List-II and choose the correct option. Includes table Includes diagram2023 · MCQ
- The maximum number of possible isomers (including stereoisomers) which may be formed on mono-bromination of 1-methylcyclohex-1-ene using and UV light is .2021 · Numerical
- Among the following, the conformation that corresponds to the most stable conformation of meso-butane-2,3-diol is2021 · MCQ
- The amount of energy required to break a bond is same as the amount of energy released when the same bond is formed. In gaseous state, the energy required for homolytic cleavage of a bond is called Bond Dissociation Energy (BDE) or Bond… Includes table Includes diagram2021 · MCQ
- The amount of energy required to break a bond is same as the amount of energy released when the same bond is formed. In gaseous state, the energy required for homolytic cleavage of a bond is called Bond Dissociation Energy (BDE) or Bond… Includes diagram2021 · MCQ
- Newman projections P, Q, R and S are shown below : Which one of the following options represents identical molecules? Includes diagram2020 · MCQ
- Which of the following structures has the IUPAC name 3-ethynyl-2-hydroxy-4-methylhex-3-en-5-ynoic acid?2020 · MCQ
- The Fischer projection of D-erythrose is shown below : D-erythrose and its isomers are listed as P, Q, R, and S in Column - I. Choose the correct relationship of P, Q, R, and S with D-erythrose from Column - II. Includes diagram2020 · MCQ