Organic Synthesis Involving Amines Questions

Reaction Pathways

Amines Worksheet
For the following multistep pathways, fill in the missing substances by drawing their skeletal formulae and state the reagents and conditions needed for the steps.
Question 1
Question 1 Pathway

State the conditions of steps 1 and 2.

Question 1 Answer Pathway

Step 1: Hydrogen halide gas OR concentrated hydrohalic acid (e.g. concentrated HCl). (NOT just ‘hydrochloric acid’ or ‘HCl’)

Step 2: Ammonia in a large excess, ethanolic conditions. (If dissolved in water, water will react with the chloropropane instead).

Question 2
Question 2 Pathway

State the conditions of steps 1 and 2.

Question 2 Answer Pathway

Step 1: HCN or KCN/NaCN in a strong acid.

Step 2: LiAlH4 dissolved in dry ether OR H2 and Ni catalyst.

Question 3
Question 3 Pathway

State the reagents and conditions for steps 1 and 2.

Question 3 Answer Pathway

Step 1: KCN or NaCN – ethanolic and heat under reflux.

Step 2: LiAlH4 dissolved in dry ether OR H2 and Ni catalyst.

Question 4
Question 4 Pathway

State the conditions of steps 1, 2, 3 and 4.

Question 4 Answer Pathway

Step 1: Heat, acid catalyst (conc H2SO4 or conc H3PO4).

Step 2: Hydrogen bromide gas or concentrated hydrobromic acid.

Step 3: Excess ammonia, heat, ethanolic conditions.

Step 4: Ethanoyl chloride, anhydrous.

Question 5
Question 5 Pathway

Step 1: Concentrated nitric acid and concentrated sulfuric acid catalyst, warm.

State the conditions of steps 2 and 3.

Question 5 Answer Pathway

Step 2: Concentrated HCl and a Sn (Tin) catalyst, followed by NaOH.

Step 3: Methanoyl chloride, anhydrous.