Organic Chemistry: Alcohols Lecture Notes

Vocabulary-style flashcards covering the classification, structure, physical properties, synthesis, and biological applications of alcohols based on Prof. R. Jagessar's lecture.

Alcohols

Organic compounds with the general formula $ROH$, where $R$ is an alkyl or aryl group.

Carbinol carbon

The specific carbon atom in an alcohol molecule that bears the hydroxyl ($-OH$) group.

Primary alcohol

An alcohol characterized by the general formula $RCH_2OH$, where the carbinol carbon is attached to one alkyl group.

Secondary alcohol

An alcohol characterized by the general formula $RCHR'OH$, where the carbinol carbon is attached to two alkyl groups.

Tertiary alcohol

An alcohol characterized by the general formula $RCR'R''OH$, where the carbinol carbon is attached to three alkyl groups.

Bond angle of Methanol ($CH_3OH$)

Measured at $108.9^\text{o}$, which is larger than water's angle due to Van der Waals repulsion between the groups.

Hybridization of Oxygen in Alcohols

The oxygen atom in the $ROH$ structure is $sp^3$ hybridised.

Hydrophobicity

The property of repelling water; in alcohols, this increases as the length of the aliphatic carbon chain increases.

Acid catalysed hydration

A mechanism that follows Markovnikov's rule to convert an alkene into an alcohol using $H_2O/H^+$.

Grignard reagent

An organometallic compound with the general formula $RMgX$ (where $X$ is a halogen) that acts as a nucleophile to attack electrophilic centres.

Hydroboration/oxidation

A two-step process using diborane $(BH_3)_2$ and hydrogen peroxide ($H_2O_2$) to convert an alkene into an Anti-Markovnikov alcohol.

Oxymercuration/Demercuration

A preparation method that converts an alkene to a Markovnikov alcohol using mercuric (II) acetate dihydrate followed by reduction with $NaBH_4$.

Lucas reagent

A reagent consisting of $HCl$ and $ZnCl_2$ used to react with alcohols; the mechanism is $S_N1$ for tertiary alcohols and $S_N2$ for primary alcohols.

Thionyl chloride ($SOCl_2$)

A halogenating source used to convert alcohols into alkyl chlorides, producing $SO_2$ and $HCl$ as side products.

Dehydration

The removal of water from an alcohol, typically achieved by treating with $H_2SO_4$ and heat to yield an alkene.

Esterification

The reaction of an alcohol with a carboxylic acid in the presence of a mineral acid to form an ester ($RCOOR'$).

Alkoxide

The species with the general formula $RO^-Na^+$ formed when an alcohol reacts with an electropositive metal like sodium.

Pyridinium chlorochromate (PCC)

A weaker oxidant used to oxidise primary alcohols to aldehydes without continuing the oxidation to a carboxylic acid.

Swern Oxidation

A chromium-free oxidation method using dimethyl sulfoxide (DMSO) and oxalyl chloride to convert alcohols into aldehydes or ketones.

Alcohol dehydrogenase (ADH)

A biological enzyme that catalyses the oxidation of ethanol into acetaldehyde in the presence of $NAD^+$.

Diol

A compound containing two hydroxyl groups on adjacent carbon atoms, such as ethylene glycol.

Fermentation

The manufacturing process of ethanol from sugar-rich sources using yeast, which also produces carbon dioxide.