26.4 More Carboxylic Acid Derivatives

Question 1

How do ammonia and amines act as nucleophiles?

Answer 1

By donating the lone pair of electrons on the nitrogen atom to an electron deficient species

Question 2

Ammonia + acyl chloride —>

Answer 2

Primary amide

Question 3

Draw the reaction between ethanoyl chloride and ammonia and name the products

Answer 3

See Pg 206

Question 4

What is a primary amide ?

Answer 4

Where there nitrogen atom is attached to 1 carbon atom

Question 5

What’s an amine?

Answer 5

A hydrocarbon chain with NH2 attached

Question 6

Primary amine + acyl chloride ->

Answer 6

secondary amide

Question 7

Draw the diagram for reaction of ethanoyl chloride + methylamine

Answer 7

See Pg 206

Question 8

How does addition occur between acyl chlorides and nucleophiles?

Answer 8

1. Lone pair on nucleophile attracted to and donated to the delta + carbon atom in C=O in acyl chloride
2. A dative covalent bond is formed between the nucleophile and the carbonyl carbon atom. The π bond of the C=O group breaks forming a negatively charged intermediate

Question 9

Leading on from the addition how does step 2 elimination occur?

Answer 9

1. A lone pair on oxygen reforms the C=O causing a chloride ion to be removed
2. A proton is then lost to complete the elimination
3. See Pg 207 for diagram