# Alcohols

## Vocabulary

### alcohol

hydrocarbon containing a hydroxyl functional group

### carbonyl

functional group in which a carbon atom is double-bonded to an oxygen atom

### dehydration

removal of water from a compound

### Dess-Martin oxidation

oxidation of a primary alcohol to produce an aldehyde or a secondary alcohol to produce a ketone using Dess-Martin periodinane (DMP)

### diol

alcohol with one additional hydroxyl group

### Grignard reagent

reagent that has the formula RMgX, where the halogen may be $-\rm{Cl}$, ${-}{\rm{Br}}$, or ${-}{\rm {I}}$

### hydration

addition of a water molecule as ${-}{\rm {H}}$ and ${-}{\rm{OH}}$ to two adjacent carbon atoms

### hydroboration-oxidation

chemical reaction that creates products with an anti-Markovnikov orientation with the hydroxyl group attached to the carbon with the least-substituted carbon

### hydrogen bond

weak intermolecular bond between a hydrogen atom of one molecule and a highly electronegative atom (usually fluorine, oxygen, or nitrogen) of a nearby molecule

### intermolecular force

attractive or repulsive force between a molecule and a nearby molecule, atom, or ion

### organometallic

compound that contains a metal bonded directly to a carbon

### organometallic reactions

nucleophilic addition reaction reaction with an organometallic reagent

### oxidation

reaction that involves the removal of an electron from an atom

### oxymercuration-demercuration

chemical reaction that creates a Markovnikov product through the addition of mercuric acetate (Hg(OAc)2) and water followed by a reducing agent

### phenol

benzene ring where a ${\rm {C{-}H}}$ bond is substituted for a hydroxyl group, giving a ${\rm {C{-}OH}}$ unit

### protecting group

group used in chemical synthesis to briefly mask the characteristic chemistry of a functional group so it will not interfere with a reaction

### pyridinium chlorochromate oxidation

oxidation of a primary alcohol to produce an aldehyde or a secondary alcohol to produce a ketone using pyridinium chlorochromate (PCC)

### reduction

reaction that involves the addition of an electron to an atom

### substitution

chemical reaction where one functional group is replaced with another functional group

### Swern oxidation

oxidation of a primary alcohol to produce an aldehyde or a secondary alcohol to produce a ketone using dimethyl sulfoxide (DMSO) and oxalyl chloride followed by addition of an organic base such as triethylamine