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Chapter 22: Problem 22

Write the structural formulas of all the esters that can be formed by ethylene glycol with formic and acetic acids. (One or both of the - OH groups of ethylene glycol can react.)

Short Answer

Expert verified
Question: List the structural formulas of all possible esters that can be formed from the reaction of ethylene glycol with formic acid and acetic acid. Answer: The possible esters are: 1. Monoformyl ethylene glycol: CH2OH-CH2OCOH 2. Diformyl ethylene glycol: CH2OCOH-CH2OCOH 3. Monoacetyl ethylene glycol: CH2OH-CH2OCOCH3 4. Diacetyl ethylene glycol: CH2OCOCH3-CH2OCOCH3 5. Formyl acetyl ethylene glycol: CH2OCOH-CH2OCOCH3

Step by step solution

01

Identify the reactants

Ethylene glycol (C2H6O2) has two hydroxyl (-OH) groups in its molecular structure. The other two reactants are formic acid (HCOOH) and acetic acid (CH3COOH), which are carboxylic acids with a carboxyl group (-COOH) that can react with the hydroxyl groups.
02

Reaction of ethylene glycol with formic acid

In this step, we can form esters by reacting ethylene glycol with formic acid. There are two possible outcomes in this scenario, i.e., either one or both of the hydroxyl groups in ethylene glycol can react with formic acid's carboxyl group: 1. One hydroxyl group reacts with formic acid's carboxyl group: CH2OH-CH2OH + HCOOH → CH2OH-CH2OCOH + H2O The ester formed is called monoformyl ethylene glycol. 2. Both the hydroxyl groups react with formic acid's carboxyl group (requires 2 molecules of formic acid): CH2OH-CH2OH + 2HCOOH → CH2OCOH-CH2OCOH + 2H2O The ester formed is called diformyl ethylene glycol.
03

Reaction of ethylene glycol with acetic acid

In this step, we can form esters by reacting ethylene glycol with acetic acid. Similar to step 2, there are two possible outcomes: 1. One hydroxyl group reacts with acetic acid's carboxyl group: CH2OH-CH2OH + CH3COOH → CH2OH-CH2OCOCH3 + H2O The ester formed is called monoacetyl ethylene glycol. 2. Both the hydroxyl groups react with acetic acid's carboxyl group (requires 2 molecules of acetic acid): CH2OH-CH2OH + 2CH3COOH → CH2OCOCH3-CH2OCOCH3 + 2H2O The ester formed is called diacetyl ethylene glycol.
04

Reaction of ethylene glycol with both formic and acetic acids

Finally, we can form a mixed ester by reacting each hydroxyl group of ethylene glycol with one molecule each of formic acid and acetic acid: CH2OH-CH2OH + HCOOH + CH3COOH → CH2OCOH-CH2OCOCH3 + 2H2O The ester formed is called formyl acetyl ethylene glycol.
05

List of all possible esters

Summarizing the results from steps 2, 3, and 4, we have the following esters that can be formed from the reaction of ethylene glycol with formic and acetic acids: 1. Monoformyl ethylene glycol: CH2OH-CH2OCOH 2. Diformyl ethylene glycol: CH2OCOH-CH2OCOH 3. Monoacetyl ethylene glycol: CH2OH-CH2OCOCH3 4. Diacetyl ethylene glycol: CH2OCOCH3-CH2OCOCH3 5. Formyl acetyl ethylene glycol: CH2OCOH-CH2OCOCH3

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