An organic compound 'A' has molecular formula C₈H₁₈ which on monobromination produced three isomeric products B, C and D, among which B and C are enantiomer whereas D is achiral. Treament of either C or D with alcoholic KOH produced some product E while B on similar treatment produced F (C₈H₁₆ ) an isomer of E as major product. Establish structure A to F.

Identification of Organic Compounds A to F

Given:

• Molecular formula: C₈H₁₈ (compound A)
• Monobromination produces three isomers: B, C, D
• B and C are enantiomers (chiral pair); D is achiral
• Treatment of C or D with alcoholic KOH produces product E
• Treatment of B with alcoholic KOH produces product F, an isomer of E (C₈H₁₆)

Explanation and structure assignment:

A: 2,3-dimethylpentane

Monobromination at:

• C-3: Forms chiral bromides B, C (enantiomers)
• C-2: Forms achiral bromide D

Treatment with alcoholic KOH leads to elimination:

• C or D produce E: 2,3-dimethyl-2-pentene
• B produces F: 2,3-dimethyl-1-pentene (isomer of E)