Aldehydes and Ketones: Hydroxynitriles

Question 1

What are hydroxynitriles?

Answer 1

• Molecules that contain a hydroxyl group (OH) and a nitrile group (CN)
• Hydroxy - OH
• Nitrile - CN

Question 2

Give the general structure of a hydroxynitrile

Answer 2

• RCH(OH)C≡N

Question 3

What is the suffix for a nitrile group?

Answer 3

• -nitrile

Question 4

How do you name hydroxynitriles?

Answer 4

• Carbon attached to nitrogen is always carbon-1
• Hydroxy- prefix for alcohol
• Then, rest is same as naming any other compound

Question 5

How are hydroxynitriles formed?

Answer 5

• By reacting aldehydes or ketones with potassium cyanide (KCN), followed by a dilute acid

Question 6

What type of mechanism occurs during the production of hydroxynitriles?

Answer 6

• Nucleophilic addition

Question 7

Give a brief overview of the nucleophilic addition mechanism during the production of hydroxynitriles

Answer 7

• Nucleophile attacks the molecule, causing an extra group (CN) to be added

Question 8

Give the cyanide ion nucleophile formula

Answer 8

• :CN

Question 9

How is a cyanide ion formed?

Answer 9

• Potassium cyanide dissociates in water to form K+ ions and CN- ions
• KCN ⇌ K+ + CN-

Question 10

Describe the mechanism steps during the production of hydroxynitriles

Answer 10

• CN- ion attacks the 𝛿+ carbon, donating a lone pair
• C=O bond breaks, electrons transferred to oxygen
• Oxygen has lone pair and negative charge
• Oxygen donates lone pair to H+ ion (from dilute acid) to form the hydroxyl group (OH)