Chapter 8

Question 1

Sn2 Mechanism

Answer 1

Two separate species collide
- bimolecular reaction
- determines rate of reaction

Question 1

Backside Attack

Answer 1

Nucleophile collides with electrophilic carbon opposite of the leaving group
- because the LG blocks the way
- result: geometry of carbon inverts

Question 2

Sn1 Mechanism

Answer 2

A single molecule breaks apart
- unimolecular reaction
- determines rate of reaction

Question 3

Sn1 Mechanism

Step 1

Answer 3

LG breaks free before nucleophile attacks
- results in a carbocation intermediate
- powerful electrophile

Question 4

Sn1 Mechanism

Step 2

Answer 4

Nucleophile attacks
- does not have to come from behind (because it is a separate step)

Question 5

Sn1 Mechanism

Step 3

Answer 5

Rapid acid-base step leading to alcohol product

Question 6

Nucleophile

Answer 6

Atom/Functional Group with a pair of electrons that can be shared

Question 7

Usual nucleophiles

Nucleophile Atoms
Nucleophile Compounds
Carbon Nucleophiles

Answer 7

Atoms: oxygen, nitrogen, and sulfur
Compounds: water, hydroxide, alcohols, phenols, amines, thiols, carboxylates (weak)
Carbons: enolate ion, cyanide ion