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(a) Give the products expected when acetic formic anhydride reacts with

(i) aniline and

(ii) benzyl alcohol

(b) Propose mechanisms for these reactions.

Short Answer

Expert verified

(a)

(b)

Step by step solution

01

(a) Role of aniline in reaction one

In this reaction, lone pair of electron of the nitrogen atom of aniline acts as a nucleophile, and it attacks the more electron deficient centre of the carbonyl carbon atom, i.e. aldehyde carbonyl

02

The reaction of acetic formic anhydride with aniline

When acetic formic anhydride react with aniline then there is the formation of N-phenyl formamide and acetic acid as a side product,In this reaction nucleophilic substitution reaction take place.

03

Role of benzyl alcohol in reaction two

In this reaction, lone pair of electron of oxygen atom of benzyl alcohol acts as a nucleophile and it attack to the more electron deficient centre of carbonyl carbon atom i.e. aldehyde carbonyl carbon.

04

The reaction of acetic formic anhydride with benzyl alcohol

When acetic formic anhydride reacts with aniline, then there is the formation of ester and acetic acid as a side product. Inthis reaction, a nucleophilic substitution reaction takes place.

05

(b) Mechanism for reaction with acetic formic anhydride and aniline

In the first step of this reaction, lone pair of nitrogen atom attacks as a nucleophile and it attack the less hindered carbonyl carbon and there is a formation of intermediate product, In the second step negative charge on the oxygen atom, form a double bond with carbon and there is elimination of acetate ion.

In the last step acetate ion abstract the proton and neutralize the nitrogen atom and there is a formation of final product.

06

The mechanism for reaction with acetic formic anhydride and benzyl alcohol

In the first step of this reaction, lone pair of oxygen atom attacks as a nucleophile and attack the less hindered carbonyl carbon, and there is a formation of an intermediate product. In the second step, the negative charge on the oxygen atom forms a double bond with carbon, and the acetate ion is eliminated.

In the last step, the acetate ion abstracts the proton and neutralizes the oxygen atom, and there is a formation of the final product.

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Most popular questions from this chapter

Suggest how you would convert trans-4-methylcyclohexanol to

(a) trans-1-chloro-4-methylcyclohexane.

(b) cis-1-chloro-4-methylcyclohexane.

Question: What do the following pKa values tell you about the electron-withdrawing abilities of nitro, cyano, chloro, and hydroxy groups?

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?

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.

Question: Show how you would synthesize the following carboxylic acids, using the indicated starting materials.

(a) hex-3-yne→propanoicacid

(b) cis-cyclodecene→decanedioicacid

(c ) iodobenzene→phenylaceticacid

(d)pentan-3-ol→2-ethylbutanoicacid

(e)o-xylene→phthalicacid

(f) allylbromide→but-3-enoicacid

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