Organic disulfide

Organic sulfur compounds are central to biochemistry. The role of thioesters as well as the sulfhydral-disulfide redox transition are both important themes.

Like the chemistry of organic phosphorus compounds, the chemistry of organic sulfur compounds doesn't get as much emphasis as it should in the traditional introductory organic chemistry curriculum given how many people take organic chemistry with the intention of pursuing a medical or biological sciences education. Organic chemistry taught with reference to biochemistry, reflecting the organic chemistry focus of the MCAT, would make sure students especially understand the chemistry of thioesters as well as oxidation-reduction reactions involving formation of disulfides from sulfhydrals.

WikiPremed Resources

Reaction of Alcohols with Thionyl Chloride
Mechanisms and explanations from the Organic Mechanisms Pocketbook

Reactions of Organic Sulfur Compounds Images
Image gallery for study with links to larger teaching JPEGs for classroom presentation

Question Drill for Organic Sulfur Compounds
Conceptual Vocabulary Self-Test

Basic Terms Crossword Puzzle

Basic Puzzle Solution

Learning Goals

Proficiency 

Understand the structural formulas and nomenclature for the range of oxidation states of organic sulfur compounds from thiols and sulfides to sulfate esters.

Be familiar with the use of thiol compounds as nucleophiles especially in the context of the biochemistry of cysteine side-chains.

Understand the mechanism by which two cysteine side chains can covalently interact in a protein to produce a disulfide.

Suggested Assignments

Review the basic terms for reactions of organic sulfur compounds using the question server. Complete the fundamental terms crossword puzzle. Here is the solution to the puzzle.

Review the web resources for reactions of organic sulfur compounds.

Conceptual Vocabulary for Organic Sulfur Compounds

Thiol
Thiols are the sulfur analogues of an alcohols.
Disulfide bond
A disulfide bond is a single covalent bond derived from the coupling of thiol groups.
Cysteine
Cysteine, one of the standard amino acids, possesses a thiol side chain. Along with methionine, it is one of the two standard amino acids containing sulfur.
Disulfide
A disulfide refers to the structural unit composed of a linked pair of sulfur atoms
Methionine
One of the standard amino acids, methionine possesses a thioether side chain. Along with cysteine, it is one of the two standard amino acids containing sulfur.
Sulfide
The term sulfide refers to several types of chemical compounds containing sulfur in its lowest oxidation number of -2.
Thioester
Thioesters are compounds resulting from the bonding of sulfur with an acyl group formed through esterification of a carboxylic acid and a thiol.
Sulfoxide
A sulfoxide is a chemical compound containing a sulfinyl functional group attached to two carbon atoms.
Dimethyl sulfoxide
The important aprotic solvent dimethyl sulfoxide (DMSO) consists of a sulfinyl group attached to two methyl groups.
Carbon disulfide
An important building block in organosulfur chemistry, carbon disulfide consists of a single carbon with double bonds to two sulfur atoms.
Thioether
A thioether is a functional group in organic chemistry which is similar to ethers but with sulfur in the place of oxygen.
Thioacetal
Thioacetals are the sulfur analogue of acetals.
Thiocyanate
Organic compounds containing the functional group SCN are called thiocyanates.
Sulfonamide
The sulfonamide functional group is a sulfone group connected to an amine group.
Carbonyl sulfide
Carbonyl sulfide can be considered to be a hybrid of carbon dioxide and carbon disulfide, having a single carbon double bonded to an oxygen atom on one side and a sulfur atom on the other, c
Pummerer rearrangement
The Pummerer rearrangement is an organic reaction whereby an alkyl sulfoxide rearranges to an alpha-acyloxy-thioether in the presence of acetic anhydride.
Johnson-Corey-Chaykovsky reaction
The Johnson-Corey-Chaykovsky reaction is a chemical reaction in which a carbonyl is converted to an epoxide by the action of a sulfonium ylide.