An optically active compound A, C6H₁0O₂, when dissolved in NaOH solution, consumed 1 equiv of base. On acidification, compound A was slowly regenerated. Treatment of A with LiAlH in ether followed by protonolysis gave an optically inactive compound B that reacted with acetic anhydride to give an acetate diester derivative C. Compound B was oxidized by aqueous chromic acid to ß-methylglutaric acid (3-methylpentanedioic acid), D. Identify compounds A, B, and C; do not specify stereochemistry. (The absolute stereochemical configurations of chiral substances cannot be determined from the data.) Draw compound A. Incorrect s Draw compound B. Incorrect t OH

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An optically active compound A, C6H₁0O₂, when dissolved in NaOH solution, consumed 1 equiv of base. On acidification,
2²
compound A was slowly regenerated. Treatment of A with LiAlH in ether followed by protonolysis gave an optically inactive
compound B that reacted with acetic anhydride to give an acetate diester derivative C. Compound B was oxidized by aqueous
chromic acid to ß-methylglutaric acid (3-methylpentanedioic acid), D. Identify compounds A, B, and C; do not specify
stereochemistry. (The absolute stereochemical configurations of chiral substances cannot be determined from the data.)
Draw compound A.
Incorrect
s
Draw compound B.
Incorrect
OH
Transcribed Image Text:An optically active compound A, C6H₁0O₂, when dissolved in NaOH solution, consumed 1 equiv of base. On acidification, 2² compound A was slowly regenerated. Treatment of A with LiAlH in ether followed by protonolysis gave an optically inactive compound B that reacted with acetic anhydride to give an acetate diester derivative C. Compound B was oxidized by aqueous chromic acid to ß-methylglutaric acid (3-methylpentanedioic acid), D. Identify compounds A, B, and C; do not specify stereochemistry. (The absolute stereochemical configurations of chiral substances cannot be determined from the data.) Draw compound A. Incorrect s Draw compound B. Incorrect OH
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