Ch 10 Notes

Question 1

Oxidation

Answer 1

lose e-; ↑C-Z bonds and/or ↓C-H bonds

Question 2

Reduction

Answer 2

gain e-; ↓C-Z bonds and/or ↑C-H bonds

Question 3

Oxidation Numbers

Answer 3

Question 4

Alcohol oxidizing reagent

Answer 4

Cr(VI)

Question 5

Preparation of Alcohols

Answer 5

S_n2

Me R-X or 1° R-X + ⁻OH

Question 6

Preparation of Ethers

Answer 6

Williamson Ether Synthesis

S_N2

Alcohol -> Alkoxide -> Ether

1. R’OH —-NaH—-> R’O⁻ + H₂
2. R’O⁻ + 1° R-X —-> R’O-R + X⁻

Question 7

Preparation of Epoxides

Answer 7

(Internal) S_n2

Halohydrin —NaH / (S_n2)—> Epoxide

Question 8

Alcohol Dehydration

Answer 8

Reverse of acid-catalyzed hydration

E1 or E2

rate: 3° >2° > 1° alcohol

use STRONG acid catalyst (H₂SO₄ or H₃PO₄)

Steps:

1. Protonation of OH group -> H₂O+
2. Lose H₂O => R+ (~shifts here if E1!!!)
3. Abstraction of H⁺ => C=C

Question 9

Zaitsev Rule

Answer 9

More substituted products = major

Question 10

Alcohol Conversion to R-X

Answer 10

Question 11

Alcohol Oxidation Path 1°

Answer 11

1° Agents: Cr(VI) Jones (strong) or KMnO₄^-

2 paths:

1. alcohol —-Cr(VI) / H₂SO₄(aq) or KMnO₄^- / ^-OH—–> aldehyde ——H₃O+—-> carboxylic acid
2. alcohol —-PCC (CrO₃/pyridine/HCl)—-> aldehyde only!

Question 12

Alcohol Oxidation Path 2°

Answer 12

Agents: Jones or PCC

Result: Ketone

Question 13

Alcohol Oxidation Path 3°

Answer 13

NOOOOO!!!

Question 14

Structure of p-toulenesulfonyl (TsCl)

Answer 14