DAT orgo - Alcohols, Ethers, and Epoxides

Add HX to alcohols (primary carbon)

SN2

Add HX to alcohols (secondary and tertiary carbon)

SN1

Pbr3 and pyridine

turn alcohols into alkyl bromides via AN SN2 REACTION, IT WILL BE OPPOSITE STEROCHEMISTRY

Socl2 and pyridine

turn alcohols into alkyl chlorides via AN SN2 REACTION, IT WILL BE OPPOSITE STEROCHEMISTRY

Mscl and pyridine

Makes alcohol into a stronger leaving group

Tscl and pyridine

Makes alcohol into a stronger leaving group

Dehydrating alcohols

uses H2So4 and H3PO₄

What do Primary alcohol dehydration undergo

E2

What do Secondary and tertiary alcohol dehydration undergo

E1

Reductions in orgo

• Gaining electrons

• Gaining bonds to hydrogen

• Losing bonds to oxygen

• Losing double or triple bonds

oxidations in orgo

• Losing electrons

• Gaining bonds to oxygen

• Losing bonds to hydrogen

  • Gaining double or triple bonds

oxidizing alcohols - primary

they get turned into carboxylic acids
UPON BEING EXPOSED TO CROMIUM REAGENTS

oxidizing alcohols - secondary

They get turned into ketones

UPON BEING EXPOSED TO CROMIUM REAGENTS

What do chromium alcohol oxidations need

Primary carbons or secondary alcohol, they need an H attached to the carbon that the OH is attached to

PCC oxidation

Turns secondary alcohols into ketones

turns primary alcohols into aldehydes

periodinane oxidation

Turns secondary alcohols into ketones

turns primary alcohols into aldehydes

Swern oxidation

accomplishes the same thing as PCC and peroxidane, but does so without using toxic chromium reagents

using DMSO, COCl2

and NEt3

William ether synthesis

SN2 mechanisms with Na k and NaH (base)

when doing williamson ether synthesis, what is important to do?

try to make the halide as close to 1’ as possible to promote SN2

If an alohol is larger than ethanol, why does it undergo william synthesis

due to the base

adding HX to ethers

Add HX, Cl Br or I and form an alkyl halide and an alcohol

What if R and R’ are 2' or 3’ in ether reactions

they proceed through SN1

What if R and R’ are 1' in ether reactions

the reaction will go through SN2

Adding HX to ethers

what if R on an ether was a phenyl

The HX would not add onto the phenyl, as SN2 reactions cannot occur on rings

Epoxidation of alkenes with peroxyacids

Epoxidizing alkenes using Sn2

alkenes are first exposed to Cl2 and H2O, and then put under basic conditions (H2O and NaOH) This deprotinates the H, causing an SN2 reaction

adding nucleophiles to epoxides under basic conditions

the nucleophile attacks the less substitued peroxide carbon

TRANS

adding nucleophiles to epoxides under acidic conditions

a Hydrogen attacks the peroxide oxygen, making the

the nucleophile attacks the more substitued peroxide carbon due to the positive charge on the nucleophile TRANS

forming trans dihydroxides under acidic conditions

forming trans dihydroxides under basic conditions