An organic compound A (C7H16O) shows both enantiomerism and diastereom...
Since, A is completely saturated, it must contain more than one chiral carbon atoms in order to show both enantiomerism and diastereomerism. Also, C on ozonolysis gives D (C
5H
10O) as one product, other product must be CH
3SHO. Hence, C must be
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An organic compound A (C7H16O) shows both enantiomerism and diastereom...
Enantiomerism and Diastereomerism of Compound A
- Enantiomerism refers to the existence of mirror-image isomers, also known as enantiomers. Enantiomers have the same molecular formula but differ in their spatial arrangement.
- Diastereomerism refers to the existence of stereoisomers that are not mirror images of each other. Diastereomers have different physical and chemical properties.
Reaction of Compound A with Na2CrO4/Dil. H2SO4
- Treatment of a pure enantiomer of compound A with Na2CrO4/Dil. H2SO4 results in the formation of compound B (C7H14O).
- The reaction involves oxidation of the alcohol group in compound A to a carbonyl group in compound B.
Dehydration of Compound A with Concentrated H2SO4
- Dehydration of compound A with concentrated H2SO4 leads to the formation of a single alkene, compound C (C7H14).
- The reaction involves the removal of a water molecule from compound A, resulting in the formation of a double bond.
Ozonolysis of Compound C followed by Work-up with Zn-H2O
- Ozonolysis of compound C followed by work-up with Zn-H2O gives compound D (C5H10O) as one of the products.
- The reaction involves the cleavage of the double bond in compound C by ozone, resulting in the formation of two carbonyl groups.
- The presence of Zn-H2O reduces one of the carbonyl groups, resulting in the formation of compound D.
Reduction of Compound D with NaBH4
- Reduction of compound D with NaBH4 gives a racemic mixture.
- NaBH4 is a mild reducing agent that can selectively reduce one of the carbonyl groups in compound D, resulting in the formation of a chiral center.
- As a result, a racemic mixture is formed, containing both the R and S enantiomers.
Reaction of Compound D with CH3CH2MgBr and Acid Hydrolysis
- Treatment of compound D with CH3CH2MgBr followed by acid hydrolysis gives a racemic mixture.
- CH3CH2MgBr is a Grignard reagent that can react with the carbonyl group in compound D, resulting in the formation of an alcohol.
- Acid hydrolysis of the intermediate alcohol results in the formation of a racemic mixture, as both the R and S enantiomers are formed.
Therefore, the correct statement regarding compound D is option C: With CH3CH2MgBr followed by acid hydrolysis, it gives a racemic mixture.