Alcohols, Ethers, and Epoxides - Organic Chemistry Flashcards

Vocabulary flashcards covering preparation methods, reactions, mechanisms, stereochemistry, and physical properties of alcohols, ethers, and epoxides based on the chemistry summary sheet.

Acid-Catalyzed Hydration

An alkene hydration method that follows Markovnikov's rule.

Oxymercuration-Demercuration (OMD)

An alkene hydration process resulting in Markovnikov addition with no carbocation rearrangement.

Hydroboration-Oxidation (HBO)

An alkene hydration reaction that results in anti-Markovnikov addition with syn stereochemistry.

Lithium Aluminium Hydride ($LiAlH_4$)

A powerful, non-selective reducing agent capable of reducing acids, esters, aldehydes, and ketones.

Sodium Borohydride ($NaBH_4$)

A selective reducing agent that reduces only aldehydes and ketones.

Grignard Addition to Formaldehyde

Reaction of formaldehyde with a Grignard reagent ($RMgX$) to form a 1° alcohol.

Grignard Addition to Ketones, Esters, & Acid Halides

Reaction of ketones, esters, or acid halides with $RMgX$ to form a 3° alcohol.

Williamson Ether Synthesis

The reaction of a 1° alkyl halide with a sodium alkoxide ($R-ONa$) via an $S_N2$ mechanism to yield symmetrical or unsymmetrical ethers.

Intermolecular Alcohol Dehydration

Dehydration of $ROH$ with concentrated $H_2SO_4$ at 140°C to form ethers.

Intramolecular Alcohol Dehydration

Dehydration of $ROH$ with concentrated $H_2SO_4$ at 170°C to form alkenes via an elimination reaction.

Dimethyl Sulphate Method

Preparation of methyl ethers using $NaOH/ROH$ and dimethyl sulphate.

Acid-Catalyzed Epoxide Ring Opening

Epoxide ring cleavage characterized by anti-attack at the more substituted carbon, causing inversion of stereochemistry at the attack site.

Base-Catalyzed Epoxide Ring Opening

Epoxide ring cleavage characterized by anti-$S_N2$ attack at the less hindered (less substituted) carbon, causing inversion at the attack site.

Pinacol-Pinacolone Rearrangement

Acid-catalyzed conversion of a vicinal diol (Pinacol) to a ketone (Pinacolone) via carbocation formation and a 1,2-group shift.

Migratory Aptitude (Pinacol Rearrangement)

The relative ease of group migration following the order: Aryl (with EDG > EWG) > H > Alkyl (3° > 2° > 1° > Me).

Pinacol Rearrangement Stereochemistry

Stereochemical outcome featuring retention at the migrating group and inversion at the migratory origin.

Halohydrin Cyclization

Base-promoted (e.g., $NaOH$) synthesis of epoxides from vicinal halohydrins operating via a Neighboring Group Participation (NGP) mechanism and intramolecular $S_N2$ reaction.

Alcohol Boiling Point Trends

Alcohols have higher boiling points than ethers, haloalkanes, and alkanes of comparable molecular weight due to hydrogen bonding; boiling point decreases with increased branching due to reduced surface area.

Alcohol Water Solubility

Property directly proportional to the number of $-OH$ groups and extent of hydrogen bonding. C1–C3 alcohols and t-butyl alcohol are completely soluble in water, but solubility decreases as side chains or molecular weight increase.