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Chapter 21: Problem 504

Hydrolysis of neutral compound (A), \(\mathrm{C}_{5} \mathrm{H}_{10} \mathrm{O}_{2}\), gave an acid (B) and an alcohol (C). C reacted with \(\mathrm{PCl}_{3}\) and was then treated with Mg. Addition of \(\mathrm{CO}_{2}\) followed by hydrolysis, yielded an acid identical to (B). Determine the structural formulas of \(\mathrm{A}, \mathrm{B}\) and \(\mathrm{C}\).

Short Answer

Expert verified
The structural formulas of A, B, and C are: A: Butyl formate: \(\mathrm{HCOOCH_2CH_2CH_2CH_3}\) B: Formic acid: \(\mathrm{HCOOH}\) C: 1-pentanol: \(\mathrm{HO(CH_2)_4CH_3}\)

Step by step solution

01

Identify possible structures of compound A

We know the molecular formula of A is C5H10O2. Here are some possible structures for this compound using the formula: 1. A diester: \(\mathrm{R-COOR'}\) 2. An ester: \(\mathrm{R-COO-R'}\) Since the hydrolysis of A produces an acid and an alcohol, option (2) is more suitable because the hydrolysis of an ester yields a carboxylic acid and an alcohol.
02

Determine the structures of acid B and alcohol C

Hydrolysis of the ester A gives an acid B and an alcohol C. Based on the molecular formula, we deduce A as: \(\mathrm{A: R-COO-R'} \) After hydrolysis, we get: \(\mathrm{B: R-COOH}\) \(\mathrm{C: HO-R'}\)
03

Examine the reactions involving alcohol C

The alcohol C reacts with PCl3, followed by treatment with Mg. This sequence of reactions suggests the Grignard reagent formation: \(\mathrm{C: HO-R'} + \mathrm{PCl}_3 \rightarrow \mathrm{R'Cl}\) \(\mathrm{R'Cl} + \mathrm{Mg} \rightarrow \mathrm{R'MgCl}\) (Grignard reagent)
04

Analyze the reaction with CO2 and hydrolysis

The Grignard reagent reacts with CO2 and then undergoes hydrolysis to produce an acid identical to B. The reactions are: \(\mathrm{R'MgCl} + \mathrm{CO}_2 \rightarrow \mathrm{R'COOMgCl}\) \(\mathrm{R'COOMgCl} + \mathrm{H}_2\mathrm{O} \rightarrow \mathrm{R'COOH} + \mathrm{Mg(OH)Cl}\) Since this acid is identical to B, this means: \(\mathrm{R'COOH = R-COOH}\)
05

Deduce the structural formulas of A, B, and C

From the information obtained in the previous steps, we deduce the following structures for A, B, and C: A: Ester: \(\mathrm{HCOOCH_2CH_2CH_2CH_3}\) (Butyl formate) B: Acid: \(\mathrm{HCOOH}\) (Formic acid) C: Alcohol: \(\mathrm{HO(CH_2)_4CH_3}\) (1-pentanol)

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