4-Bromoacetanilide Synthesis. Why is it necessary to acylate aniline prior to br

Question

4-Bromoacetanilide Synthesis. Why is it necessary to acylate aniline prior to bromination? 2. a What is meant by the terms: nucleophile and electrophile? b) In this reaction, indicate which reagent is a nucleophile and which is an electrophile. 3. Given a carbon-13 nmr spectrum, how would you be able tell the difference between acetanilide and the pure para-bromoacetanilide you just synthesized? 4. If the synthesis of para-bromoacetanilide also provided a small amount of ortho-bromoacetanilide and that your recrystallization did not work as anticipated, how would that influence your melting point (and melting point range)?

Explanation / Answer

1. To stop multibromination rather to do only mono bromination in the para position , one must block aniline (ortho bromination also stops due to presence of bulky group).

2. a). Nucleohiles are electron rich species attacks to electron deficient centres. Electrophiles are electron deficient so also loving species, loves to react with nucleophilic.

b). Acetanilide is nucleophile and Br2 is electrophile.

3. The peaks of acetanilide are at about 169, 138, 128, 124, 120, 24 whereas for brominated product the peaks are at about 24, 114, 121, 131, 138, 168

4. 4-Bromoacetanilide has higher m.p(1660 C) than 2-Bromoacetanilide(990C). So in the mixture the mixed melting point will be always less than the indivisual component.

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