Orgo II Exam 2

Oxidation of Alcohols

PCC for primary -OH → aldehyde

PCC, Jones reagent, Nacr2O7/H2SO4/H2O for secondary -OH → ketone

Ozonolysis

Has to be symmetrical to start with

1. O3

2. Me2S

→ 2 products; breaks original symmetry and replaces the = symmetry line with O for EACH product

Addition to Benzene rings

2 options:

• R—=O—Cl, AlCl3 → Ketone

• CO/HCl, AlCl3/CuCl → aldehyde

Alkynes → carbonyls

start with: R—C≡C—H

2 options:

• HgSO4/H2O, H2SO4 → ketone

• 1. Sia2BH 2. H2O2/-OH → aldehyde

Reduction of Esters

start with: R—=O—OR

• DIABALH, -78 (have to say it’s cold) → R—=O—H

ACETAL (review on paper)

• OCH3-OCH3 OR 2ROH, TSO-H (solvent)

  • will need to proton transfer

• 2 options at the end

• Zn, HCl (goes back to aldehyde/ketone)

• NH2NH2/KOH (protects ring and removes carbonyl)

Carboxylic Acid → ketone

• 2 equivalents of gringard

  • 1. R-MgBr (2eq) 2. H+

• makes original OH into an R group

Mechanism: Nucleophilic Addition **REVIEW ON PAPER

uses Gringard 2 eq. (will attack OH, then C=O in the 2nd gringard)

Mechanism: Acidic Workup

uses H-O(+)H2 so many times lol

Nitrile → Ketone

R—C≡N

• 1.R-MgBr 2.H+

• Review partial mechanism on paper

→ R—=O—R’

reducing acid chloride to aldehydes

CH3—=O—Cl

• LTBAH

  • selectively reduces

CH3—=O—H

Wittig Rxn; Product always has to be

trans

Wittig Reaction **REVIEW ON PAPER

Aldehyde/ketone + ylide