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Chapter 20: Q13P. (page 1062)

Most of the Fischer esterification mechanism is identical with the mechanism of acetal formation. The difference is in the final step, where a resonance-stabilized carbocation loses a proton to give the ester. Write mechanisms for the following reactions, with the comparable steps directly above and below each other. Explain why the final step of the esterification (proton loss) cannot occur in acetal formation, and show what happens instead.

Short Answer

Expert verified

In the formation of acetal from aldehyde, the loss of H+cannot take place to form carbonyl, and in the formation of ester from acid, the loss of H+ takes place to form carbonyl.

Step by step solution

01

Fischer esterification

Fischer esterification is the conversion of carboxylic acid to ester, and this reaction takes place in the presence of a strong acid and excess alcohol.The solvent used in these reactions is methanol or ethanol.

02

Mechanism of the reaction

The major difference between these two reactions is the loss of H+. In the formation of acetal from aldehyde, the loss of H+ cannot take place to form carbonyl, and in the formation of ester from acid, the loss of H+ takes place to form carbonyl.

Mechanism of both reactions

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Most popular questions from this chapter

Question: Arrange each group of compounds in order of increasing acidity.

  1. phenol, ethanol, acetic acid
  2. p-toluenesulfonic acid, acetic acid, chloroacetic acid
  3. benzoic acid, o-nitrobenzoic acid, m-nitrobenzoic acid
  4. butyric acid, 伪-bromobutyric acid, 尾-bromobutyric acid

Show how you would accomplish the following syntheses efficiently (you may use any necessary reagents).

(a)trans-1-产谤辞尘辞产耻迟-2-别苍别鈫�trans-pent-3-enoic acid (two ways)

(b)hex-3-ene鈫抪ropanoic acid

(c) but-2-enal鈫抌ut-2-enoic acid

(d) hexanoic acid鈫抙exanal

(e)

(f)

(g)

(h)

Show how you would accomplish the following multistep syntheses using the indicated starting material and any necessary reagents.

(a) hept-6-en-1-ol caprolactone

(b) methoxybenzenep-methoxybenzamide

(c)

(d)

Gallic acid Mescaline

Question: Rank the compounds in each set in order of increasing acid strength.

(a)CH3CH2COOH,CH3CHBrCOOH,CH3CBr2COOH

(b) CH3CH2CH2CHBrCOOH,CH3CH2CHBrCH2COOH,CH3CHBrCH2CH2COOH

(c)

,CH3CH2COOH,

Phosgene is the acid chloride of carbonic acid. Although phosgene was used as a war gas in World War I, it is now used as a reagent for the synthesis of many useful products. Phosgene reacts like other acid chlorides, but it can react twice.

(a) Predict the products formed when phosgene reacts with excess propan-1-ol.

(b) Predict the products formed when phosgene reacts with 1 equivalent of ethanol, followed by 1 equivalent of aniline.

(c) Iso-butyloxycarbonyl chloride is an important reagent for the synthesis of peptides and proteins. Show how you would use phosgene to synthesize iso-butyloxycarbonyl chloride.

Isobutyloxycarbonyl chloride
See all solutions

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