ORGO 2: EXAM 2

Reactions of Alcohols, Ketones and Aldehydes

What is a ketone?

An organic compound that has a C=O with 2 R-groups on the C.

What is an aldehyde?

An organic compound that has a C=O with 1 R-group and 1 H on the C.

What is the simple definition of an oxidation reaction?

Loss of electrons

What are the 3 methods to oxidize an alcohol? What are the reagants?

1. Jones Oxidation

   • Na₂Cr₂O₇, H₂SO₄

   • CrO₃, H₂SO₄

   • These reagents form H₂CrO₄ in the flask (highly reactive species)

2. PCC

   • PCC (Pyridinium-chloro-chromate)

3. Swern Oxidation

   • (CoCl)₂, Et₃N, DMSO

What are the reagents to do a Jones Oxidation?

These both form H₂CrO₄ in the flask (highly reactive species)

• Na₂Cr₂O₇, H₂SO₄

• CrO₃, H₂SO₄

Jones Oxidation of a primary alcohol results in what product?

Carboxylic Acid

PCC Oxidation of a primary alcohol results in what product?

Aldehyde

Oxidation of a secondary alcohol results in what product?

Ketone

Oxidation of a tertiary alcohol results in what product?

No product / No RXN

How is the Swern Oxidation method different from Jones and PCC Oxidation?

Swern Oxidation does not use transition metals

What are the reagents of Swern Oxidation?

(COCl)₂, Et₂N, DMSO

What is a carbonyl?

C=O group

What are 3 methods to do addition to a carbonyl? What are examples of reagents?

1. Alkyne nucleophilic addition

   1. R-C≡C:⊖ , Na⊕

   2. H₃O⊕

2. Grignard addition

   1. R’-MgBr

   2. H₃O⊕

3. Hydride addition

   • LiAlH₄ OR NaBH₄