MS 917 - Alcohol and Carbonyl Redox Submitted by Matt on August 6, 2011.

Textbook and Chapter: Carey and Giuliano 8th Ed. (2010), Chapter 15

Keywords: alcohols, hydride reduction, oxidation

Description: Goes over how alcohols can be oxidized to form aldehydes/ketones and carboxylic acids, which can be transformed further using Grignard reagents, hydride reagents such as NaBH4, and by performing Fischer esterification. Includes several synthesis problems involving carbonyls and epoxides. Also includes an NMR based problem.

Total Problems: 5

Problem # 723

Show how to prepare each compound from vinyl benzene.

How would you prepare the methyl ester of each compound?

Problem # 679

Compound A (C5H12O) is oxidized using aqueous chromium (Jones reagent) to compound B (C5H10O2), which is then treated with methanol under acidic conditions to yield compound C (C6H12O2) and water.

The 1H NMR of compound C is shown below. Determine the structures of compounds A, B, and C.

Problem # 673

Show how each compound can be prepared from an alkene containing 3 carbons (or less).

Each answer will involve the reaction of a Grignard with either a carbonyl or epoxide.

Note: epoxides are prepared from alkenes using a peroxy acid (epoxidation) such as mCPBA.