Home
Class 11
CHEMISTRY
Meso- and racemic -2,3-dibromobutane on ...

Meso`-` and racemic `-2,3-`dibromobutane on reaction with `Nal` in acetone give `:`

A

`E-`But`-2-`ene and `Z-`But`-2-`ene, respectively

B

`Z-`But`-2-2`ene and `E-`But`-2-`ene, respectively

C

Both give `E-`But `-2-`ene

D

Both give `Z-`But`-2-`ene

Text Solution

AI Generated Solution

The correct Answer is:
To solve the problem of what meso- and racemic-2,3-dibromobutane yield when reacted with NaI in acetone, we can follow these steps: ### Step 1: Understand the Structures - **Meso-2,3-dibromobutane** has a plane of symmetry, making it achiral. The bromine atoms are on the same side (erythro configuration). - **Racemic-2,3-dibromobutane** consists of two enantiomers (mirror images) where the bromines are on opposite sides (threo configuration). ### Step 2: Reaction Mechanism - The reaction of 2,3-dibromobutane with NaI in acetone involves an **anti-elimination** mechanism. This means that the bromine atoms will be removed in such a way that they are eliminated from opposite sides of the molecule. ### Step 3: Analyze the Meso Form - For **meso-2,3-dibromobutane**, when subjected to anti-elimination, the bromines will be removed from opposite sides, resulting in the formation of a **trans-alkene** (E form). The product will have the structure: \[ \text{C} \equiv \text{C} \text{CH}_3 \text{CH}_3 \text{H} \text{H} \] ### Step 4: Analyze the Racemic Form - For **racemic-2,3-dibromobutane**, the two enantiomers will also undergo anti-elimination. However, since they are enantiomers, the product will be a **cis-alkene** (Z form). The structure will be: \[ \text{C} \equiv \text{C} \text{CH}_3 \text{H} \text{H} \text{CH}_3 \] ### Step 5: Conclusion - Therefore, the meso-2,3-dibromobutane will yield a **trans-alkene (E form)**, and the racemic-2,3-dibromobutane will yield a **cis-alkene (Z form)**. ### Final Answer - The products of the reactions are: - Meso-2,3-dibromobutane → **E form** - Racemic-2,3-dibromobutane → **Z form**

To solve the problem of what meso- and racemic-2,3-dibromobutane yield when reacted with NaI in acetone, we can follow these steps: ### Step 1: Understand the Structures - **Meso-2,3-dibromobutane** has a plane of symmetry, making it achiral. The bromine atoms are on the same side (erythro configuration). - **Racemic-2,3-dibromobutane** consists of two enantiomers (mirror images) where the bromines are on opposite sides (threo configuration). ### Step 2: Reaction Mechanism - The reaction of 2,3-dibromobutane with NaI in acetone involves an **anti-elimination** mechanism. This means that the bromine atoms will be removed in such a way that they are eliminated from opposite sides of the molecule. ...
Promotional Banner

Topper's Solved these Questions

  • ALKENES AND ALKADIENES

    CENGAGE CHEMISTRY ENGLISH|Exercise Archives(ASSERTION-REASIOING)|4 Videos
  • ALKENES AND ALKADIENES

    CENGAGE CHEMISTRY ENGLISH|Exercise Fill in the Blanks|3 Videos
  • ALKENES AND ALKADIENES

    CENGAGE CHEMISTRY ENGLISH|Exercise Multiple Correct Answer Type|41 Videos
  • ALKANES AND CYCLOALKANES

    CENGAGE CHEMISTRY ENGLISH|Exercise Archives|13 Videos
  • ALKYNES

    CENGAGE CHEMISTRY ENGLISH|Exercise Exercises (Archives - Analytical and Desriptive Type)|4 Videos

Similar Questions

Explore conceptually related problems

The racemic -2,3- dibromopentane on reaction with KI in acetone give :

A partially racemised (+2) 2-Bromooctane on reaction with aq. NaOH in acetone gives an alcolhol with 80% inversion and 20% racemisation . Find out the rate expression of the reaction.

A partially racemised (+) - 2-bromo-octane (2^@ RX) on reaction with aq. NaOH in acetone gives an alcohol with 80 % inversion and 20 % racemisation. What is the percentage of back-side attack ?

In the following questions, a statement of assertion (A) is following by a statement of reason (R ) A : Meso -2, 3 - dibromobutane on reaction with Zn/ether gives trans but -2 ene . R : Zn/ether gives anti elimination .

What happens when (+)2- iodobutane is treated with Nal in acetone?

Calculate the percentage of SN^(-1) product, if (R )-2 -Chloro butane on reaction with NaOH//H_(2)O and acetone gives 98% inverted product.

Statement-I: Optically active 2-idoibutane on treatment with NaI in acetone undergoes racemisation. Because Statement-II: Repeated Walden inversions on the reactant and its product evantually gives a racemic mixure.

The Grignard reagent, on reaction with acetone, forms :

Assertion : trans -2- Butene on reaction with Br_(2) gives meso -2,3- dibromobutane. Reason : The reaction involves syn - addition of bromine.

Knowledge Check

  • The conversion of2, 3-dibromobutane to 2-butene with Zn is

    A
    Redox reaction
    B
    `alpha`- Elimination
    C
    `beta`- Elimination
    D
    Both `alpha` - elimination and redox reaciton