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Chapter 20: Q12P b. (page 1061)

Question:

  1. The Key Mechanism for Fischer esterification omitted some important resonance forms of the intermediates shown in brackets. Complete the mechanism by drawing all the resonance forms of these two intermediates.
  2. Propose a mechanism for the acid-catalyzed reaction of acetic acid with ethanol to give ethyl acetate.
  3. The Principle of Microscopic Reversibility states that a forward reaction and a reverse reaction taking place under the same conditions (as in equilibrium) must follow the same reaction pathway in microscopic detail. The reverse of the Fischer esterification is the acid-catalyzed hydrolysis of an ester. Propose a mechanism for the acid-catalyzed hydrolysis of ethyl benzoate, PhCOOCH2CH3.

Short Answer

Expert verified

Answer

(b). The mechanism for the acid-catalyzed reaction of acetic acid with ethanol is:



Step by step solution

01

Acid-catalyzed reaction

Acid-catalyzed reaction is a reaction catalyzed by acid, and these acid catalysts accelerate the chemical reaction.It facilitates the nucleophilic attack of alcohol at the carbonyl carbon of a carboxylic acid.

02

Mechanism of acid-catalyzed reaction

(b) This mechanism has six steps. It starts with proton on (resonance stabilization) and ends with proton off.

In step A, a proton is added, and resonance structures are formed.

In step B, the nucleophile attacks the carbon.

In step C, proton off occurs.

In step D, a proton is added again.

In step E, leaving of leaving group and resonance structures are formed.

In step F, proton off occurs.

The mechanism for acid-catalyzed reaction

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Most popular questions from this chapter

Question: Give both IUPAC names and common names for the following compounds.

(a) phCH2COOH

(b) phCO2Na

(c) (CH3)2 CHCHCICOOH

(d) HOOC (CH2)4CO2H

(e) (CH3)2 CHCH2COOK

(f) CH3 CH(NH2) COOH

(g)

(h)

(i)

Show how you would distinguish among the following three compounds

  1. Using infrared spectroscopy and no other information.
  2. Using proton NMR spectroscopy and no other information.
  3. Using, including DEPT, and no other information.

Substituent effects: resonance and induction.

(a)When the methoxy group is in the meta position inB, is the acid stronger or weaker than inA? Is the methoxy group in the meta position electron-donating or withdrawing?

(b)When the methoxy group is in the para position inC, is the acid stronger or weaker than inA? Is the methoxy group in the para position electron-donating or withdrawing?

(c)How can this apparent contradiction be explained? Which effect is stronger for methoxy?

(d)When the fluoro group is in the meta position inE, is the acid stronger or weaker than inD? Is the fluoro group in the meta position electron-donating or withdrawing?

(e)When the fluoro group is in the para position inF, is the acid stronger or weaker than inD? Is the fluoro group in the para position electron-donating or withdrawing?

(f)Compare the results of the fluoro group with those of the above methoxy group. What must be different about the relative strength of the resonance and inductive effects for fluoro compared with methoxy?

Classify each hydrogen atom in the following compounds as primary (10),secondary(20) , or tertiary(30).

(a) butane

(b) isobutane

(c) 2-methylbutane

(d) cyclohexane

(e) norbornane (bicyclo heptane)

For each compound,

  1. Classify the nitrogen containing functional groups.
  2. Provide acceptable name

(a)

(b)

(c)

(d)

(e)

(f)

(g)

(h)
See all solutions

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