Reagents for Alcohol Rxns (Ch12)

A set of flashcards covering nomenclature, oxidation states, and various reagents/transformations related to Alcohols as detailed in Chapter 12 notes.

NaH (Sodium hydride)

A very strong base used to deprotonate alcohols to give an alkoxide ion ($R-O^-$).

Na (Sodium metal)

Reacts with alcohols to liberate $H_2(g)$ and produce an alkoxide ion.

Sodium borohydride ($NaBH_4$, MeOH)

A reagent that reduces ketones or aldehydes to alcohols.

Lithium aluminum hydride (1. $LiAlH_4$, 2. $H_3O^+$)

A reagent that reduces ketones, aldehydes, esters, and carboxylic acids to alcohols.

$H_2$, Pt

Commonly reduces alkenes/alkynes to alkanes, and can also reduce ketones or aldehydes to alcohols.

Grignard Reagent ($RMgX$)

Reacts with aldehydes to form 2° alcohols, ketones to form 3° alcohols, and esters to form 3° alcohols (requires excess reagent).

TMSCl / $Et_3N$

Used to protect alcohols by converting $ROH$ to $ROTMS$, preventing reaction with Grignard reagents.

TBAF

Used to un-protect alcohols by converting $ROTMS$ back to $ROH$.

HX (X=Cl or Br)

Strong acids and strong nucleophiles used to convert alcohols to alkyl bromides or alkyl chlorides.

TsCl, pyridine

Converts an alcohol ($OH$) into a tosylate ($OTs$) to create a better leaving group.

$$PBr_3$$

Converts 1° or 2° alcohols into alkyl bromides via $S_N2$ mechanism, resulting in an inversion of configuration at chiral centers.

$SOCl_2$, pyridine

Converts 1° or 2° alcohols into alkyl chlorides via $S_N2$ mechanism, resulting in an inversion of configuration at chiral centers.

HCl, $ZnCl_2$

Reagent conditions used to convert alcohols into alkyl chlorides.

$Na_2Cr_2O_7$, $H_2SO_4$, $H_2O$

Produces chromic acid, a strong oxidizing agent that converts 1° alcohols to carboxylic acids and 2° alcohols to ketones.

PCC, $CH_2Cl_2$

An oxidizing agent that converts 1° alcohols into aldehydes and 2° alcohols into ketones.

DMP, $CH_2Cl_2$

An oxidizing agent that converts 1° alcohols into aldehydes and 2° alcohols into ketones.

Swern Oxidation (1. DMSO, $(COCl)_2$, 2. $Et_3N$)

A process that converts 1° alcohols into aldehydes and 2° alcohols into ketones.