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Chapter 22: Q64. (page 918)

Question: What carboxylic acid and alcohol are needed to prepare each ester by Fischer esterification?

a.

b.

Short Answer

Expert verified

Answer

a.

Parent compounds of ester a

b. Parent compounds of ester b

Step by step solution

01

Step-by-Step Solution Step 1: Fischer esterification

Esters are synthesized from alcohol and carboxylic acids.

Carboxylic acids are inactive towards esterification, and therefore, require activation. Therefore, catalysts are used.

Catalysts can be acids or bases. If the catalyst used is a mineral acid, the esterification reaction is called Fischer esterification.

In this method, the acid and alcohol refluxed in the presence of the acid.

02

Identifying the parent acid and alcohol of an ester

Consider an ester RCOOR.

In this compound, the carbonyl part (RCO) comes from the carboxylic acid, and the alkoxy part (R’O) comes from the alcohol.

Therefore, to find the parent acid and alcohol of an ester, the C-O bond in ester is broken, and the structure of the corresponding acid and alcohol is completed.

03

Identifying acid and alcohol needed to prepare given esters

a. The given ester is cyclohexyl benzoate.

Therefore, the acid and alcohol required to prepare this ester are shown below.

Retroanalysis of cyclohexyl benzoate

b. The given ester is isobutyl isobutyrate.

Therefore, the acid and alcohol required to prepare this ester are given below.

Retroanalysis of isobutyl isobutyrate

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Most popular questions from this chapter

Question: (a) Give an acceptable name for each compound. (b) Draw the organic products formed when A or B is treated with each reagent: [1]H3O+;[2]-OH,H2O;[3]CH3CH2CH2MgBr(excess), then H2O; [4] LiAlH4,ThenH2O, then .

Question: With reference to the structures of acetylsalicylic acid (aspirin, Chapter 2 opening molecule) and acetaminophen (the active ingredient in Tylenol), explain why acetaminophen tablets can be stored in the medicine cabinet for years, but aspirin slowly decomposes over time.

Question: How would the compounds in each pair differ in their IR spectra?

a.

b.

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d.

Question: Draw the structure of Kodel, a polyester formed from 1,4-dihydroxymethylcyclohexane and terephthalic acid. Explain why fabrics made from Kodel are stiff and crease-resistant.

Question: What product is formed when the esters in ginkgolide B, the chapter-opening molecule, are hydrolyzed in aqueous acid? Indicate the stereochemistry of all stereogenic centers.

Ginkgolide B
See all solutions

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