Alcohol, Ether And Epoxide Reactions

Question 1

Acid catalyzed dehydration of a 1° alcohol

Answer 1

Mechanism: E2
Rearrangement: No
Reagents: H₃O⁺, H₂SO₄/ Δ

Since it goes through an E2 mechanism, no carbocation is formed and therefore no rearrangement can occur

Question 2

Na₂Cr₂O₇ or CrO₃ , H₂SO₄

Answer 2

Strong oxidizing agent
Reduces:
› 1° alcohol —> carboxylic acid
› 2° alcohol —> ketone
› 3° alcohol —> no reaction

Question 3

Ether cleavage: S_n2 mechanism

Answer 3

Nucleophile adds to less substituted side
Aryl, vinyl, methyl and 1° ethers

Question 4

Ether cleavage: S_n1 mechanism

Answer 4

Nucleophile adds to more substituted side
For: 2°, 3°, benzyl and allyl ethers

Question 5

Epoxied opening: acidic conditions

Answer 5

Nucleophile attacks most substituted side
Product: trans diol

Question 6

Epoxied ring opening: basic conditions

Answer 6

Nucleophile adds to least substituted side
Product: trans diol