Organic conversion

Ethanol to ethanamine

2 steps: substitution, then substitution

Class 12, Chapter 6 Haloalkanes and Haloarenes

Step 1: Ethanol to chloroethane: SOCl₂.
Step 2: Chloroethane to ethanamine: NH₃ (excess), ethanolic, sealed tube, 373 K.

Alternative routes (4)

Ethanol → Bromoethane → Ethanamine
1. Ethanol to bromoethane: red P + Br₂ (PBr₃).
2. Bromoethane to ethanamine: NH₃ (excess), ethanolic, sealed tube, 373 K.
Ethanol → Ethene → Bromoethane → Ethanamine
1. Ethanol to ethene: conc. H₂SO₄, 443 K.
2. Ethene to bromoethane: HBr.
3. Bromoethane to ethanamine: NH₃ (excess), ethanolic, sealed tube, 373 K.
Ethanol → Ethene → Chloroethane → Ethanamine
1. Ethanol to ethene: conc. H₂SO₄, 443 K.
2. Ethene to chloroethane: HCl.
3. Chloroethane to ethanamine: NH₃ (excess), ethanolic, sealed tube, 373 K.
Ethanol → Bromoethane → Nitroethane → Ethanamine
1. Ethanol to bromoethane: red P + Br₂ (PBr₃).
2. Bromoethane to nitroethane: AgNO₂.
3. Nitroethane to ethanamine: H₂, Pd (or Sn + HCl, or Fe + HCl).

Why these reagents

Reagent and reason, step by step

Step 1: Ethanol to chloroethane: SOCl₂ Thionyl chloride gives the pure alkyl chloride because SO₂ and HCl leave as gases.
Step 2: Chloroethane to ethanamine: NH₃ (excess), ethanolic, sealed tube, 373 K Ammonolysis gives the amine with the same carbon count.

Questions

How many steps does it take to convert ethanol to ethanamine?

2 steps: Ethanol, then chloroethane, then ethanamine.

Which named reaction is used to convert ethanol to ethanamine?

None of the steps has a name. They are substitution and substitution, so write the reagent and the condition for each step.

What is the reagent for step 1 of ethanol to ethanamine?

Ethanol to chloroethane: SOCl₂. Thionyl chloride gives the pure alkyl chloride because SO₂ and HCl leave as gases.