Organic chemistry 2- reactions-factoids

Monochlorination of methane

Monobromination of ethane

Peroxide formation

Addition of HBr to an alkene in the presence of a peroxide

Peroxide plays a role in allylic brominations by easily forming radicals, which then react with NBS to generate bromine radicals

Sn1 reaction of an alcohol

only for tertiary and secondary alcohols

Sn2 reaction of alcohol

Only for primary alcohols

Converting an alcohol to an alkyl bromide using PBr3

Converting an alcohol to an alkyl chloride using SOCl2

Converting an alcohol to a sulfonate ester

E1 dehydration of an alcohol

secondary and tertiary

E2 dehydration of alcohol

primary

Oxidation of an alcohol

Ether cleavage: Sn1 reaction

Ether cleavage: Sn2 reaction

Ethers are cleaved with an Sn1 reaction unless the stability of the carbocation requires it to be an Sn2

Nucleophilic substitution reaction of Epoxides
ACIDIC CONDITIONS

Under acidic conditions the nucleophile prefers to attack the more substituted ring carbon

Nucleophilic substitution reaction of Epoxides
BASIC/NEUTRAL CONDITIONS

Cis Glycol formation

Arene Oxide Rearrangement

NIH shift

Bonus: what decides carcinogenity of arene oxides

The less stable the carbocation upon ring opening, the more carcinogenic it is.

Hofmann-Elimination of a quartenary ammonium

Anti-zaitsev elimination: proton removed from carbon with least protons
This is because that creates the most stable alkene transition state.

Thiols are the analogues of what?

alcohols

Sulfides are the analogues of what?

ethers

Sulfonium ions are the analogues of what

Quart. ammonium ions

The weaker the base the?

better the leaving group

Reaction of an acyl chloride with a negative nucleophile

• tetrahedral intermediate is formed

• weakest base leaves

Reaction of an acyl chloride with a neutral nucleophile

Transesterification

The conversion of one ester into another ester

Mechanism for acid-catalyzed ester hydrolysis

Ester hydrolysis with tertiary alkyl group

Hydroxide promoted ester hydrolysis

Acid catalyzed amide hydrolysis

Acid cataylsed hydrolysis of a nitrile

Reaction of an acid anydride with a alcohol

Grignard reagent

Magnesium halide that makes the carbon a nucleophile

Formaldehyde with grignard

Creates a primary alcohol

Aldehyde with grignard

Creates a secondary alcohol

Ketone with grignard

Creates a tertiary alcohol

Ester with grignard reagent

Mechanism for aldehyde/ketone with hydride ion

M

Mechanism for acyl chloride with hydride ion

Mechanism for ester with hydride ion

Me

Mechanism for carboxylic acid with hydride ion

Mechanism forn substitued amide with hydride ion

Mechanism for imine formation

Mechanism for enamine formation

Mechanism acid catalyzed hydrate formation

Mechanism acid catalyzed acetal formation

Baeyer villiger oxidation

In the Baeyer villiger mechanism, what R group is most likely to migrate to the oxygen?