Organic Chemistry 13 - Ethers, Epoxides, Thiols and Sulfides

Ether synthesis

acid - catalyzed addition of an alcohol

alkoxymercuration-demercuration

Sn1

Williamson Ether synthesis (deprotonation step)

Williamson Ether synthesis (Sn2 step), primary carbon chosen since Sn2 is easier with a primary carbon

Acidic Ether Cleavage

Phenyl Acidic Ether Cleavage

What is the principle between either SN1 or SN2 for acidic ether cleavage?

Sn1 for 3 or 2 carbons; Sn2 for 1 carbons

Sn2 synthesis of epoxides

Peroxyacid Addition to Alkenes

Sharpless epoxidation (+)

Sharpless epoxidation (-)

Strong Nucleophile ring-opening of epoxides (1)

In a strong nucleophile ring opening of an epoxide, which side does it attack?

The less substituted side

Strong Nucleophile ring-opening of epoxides (2, protonation step)

Acidic catalyzed nucleophile reaction

What order does the nucleophile prefer to attack in acidic catalyzed nucleophile reaction?

3 >1 >2

Sn2 thiol synthesis

Oxidation of Thiols to form Disulfude

Sulfide synthesis through Sn2

Synthesis of Sulfide Alkylating Agent (Sn2)

Synthesis of sulfide from alkylating agent

Oxidation of sulfide

oxidation of sulfoxide to sulfone

oxirane

A cyclic ether containing a three-membered ring system. Also called an epoxide.

ether

A compound with the structure R―O―R.

symmetrical ether

An ether (R―O―R) where both R groups are identical.

mercapto group

An SH group.

polyether

A compound containing several ether groups.

unsymmetrical ether

An ether (R―O―R) where the two R groups are not identical.

alkoxy substituent

An OR group.

alkoxymercuration-demercuration

A two-step process that achieves Markovnikov addition of an alcohol (H and OR) across an alkene. The product of this process is an ether.

alkylthio group

An SR group.

acidic cleavage

A reaction in which bonds are broken in the presence of an acid. For example, in the presence of a strong acid, a dialkyl ether is converted into two alkyl halides.

Williamson ether synthesis

A method for preparing an ether from an alkoxide ion and an alkyl halide (via an SN2 process).

sulfide

A compound that is similar in structure to an ether, but the oxygen atom has been replaced with a sulfur atom. Also called a thioether.

crown ether

A cyclic polyether whose molecular model resembles a crown.

disulfide

A compound with the structure R―S―S―R.

sulfone

A compound that contains a sulfur atom that has double bonds with two oxygen atoms and is flanked on both sides by R groups.

thiols

Compounds containing a mercapto group (SH).

thiolate

The conjugate base of a thiol.

Sharpless asymmetric epoxidation

A reaction that converts an alkene into an epoxide via a stereospecific pathway.

sulfoxide

A compound containing an S═O bond that is flanked on both sides by R groups.