Organic Chemistry Alcohols, Ethers, and Epoxides (DAT)

Hydroxyl FG are ___ (good/bad) leaving groups

bad

R-OH + HX —>

R-X

Alcohols can be converted to alkyl halides by reacting them with a hydrophalic acid such as

HI, HBr, HCl

If a tertiary or secondary alcohol reacts with HX, it does so in a ___ mechanism

SN1

If a primary alcohol reacts with HX, it does so in a ___ mechanism

SN2

Secondary alcohol + PBr3, pyrimidine —>

inverted Br

Secondary alcohol + SOCl2, pyrimidine —>

inverted Cl

Secondary alcohol + MsCl, pyrimidine —>

same OMs

Secondary alcohol + TsCl, pyrimidine —>

same OTs

Alkyl halide + -CN —> ___ stereochemistry

inverted

Secondary alcohol + H3O+, heat —>

alkene

The following reagents are used in a ___ synthesis reaction:

1. NaH or NaNH2

2. Alkyl halide

williamson ether

Williamson Ether reactions work best with a ___ or ___ hallide

methyl, primary

Williamson ether reactions join the two molecules via the

oxygen

primary alcohol + strong acid —>

symmetrical ether

Ether + HBr —>

separates ether into XR and XR

Ether + HI —>

separates ether into XR and XR

Ether bound to aryl/vinyl group + HBr/HI —>

alcohol and alkyl halide

General name for the structure

vinyl halide

General name for the structure

aryl halide

If an epoxide is opened in basic conditions, the nucleophile will attack the ___ substituted carbon

less

If an epoxide is opened in acidic conditions, the nucleophile will attack the ___ substituted carbon

more

When epoxides are opened, regardless of if under basic or acidic conditions, the OH and nucleophile are added ___ (syn/anti)

anti