Aldehydes, Ketones & Amines Flashcards

A set of vocabulary-style flashcards covering the reactivity, oxidation/reduction, and specific reactions of aldehydes, ketones, and amines based on the lecture transcript.

Aldehyde Reactivity

More reactive than ketones due to less steric hindrance and a larger partial positive charge.

PCC or Dess-Martin periodinane

Reagents used to oxidize a $1^{\circ}$ alcohol to an aldehyde.

$NaBH_4$ Reduction

A reagent that reduces an aldehyde to a $1^{\circ}$ alcohol or a ketone to a $2^{\circ}$ alcohol; the process is not reversible.

$LiAlH_4$ Reduction

A reagent that reduces aldehydes and ketones to alcohols; the process is not reversible.

Grignard reagent ($RMgX$)

A reagent used to form new $C-C$ bonds with carbonyls.

Formaldehyde + Grignard

A chemical reaction that yields a $1^{\circ}$ alcohol.

Aldehyde + Grignard

A chemical reaction that yields a $2^{\circ}$ alcohol.

Ketone + Grignard

A chemical reaction that yields a $3^{\circ}$ alcohol.

Cyanohydrin

A molecule containing an $OH$ and a $CN$ group on the same carbon, formed irreversibly using $CN^-$ (cyanide).

Hydrate

A carbon bearing two $OH$ groups; its formation is reversible and typically favors the carbonyl form in equilibrium.

Formaldehyde and trichloroacetaldehyde

Specific aldehydes that readily form hydrates.

Tollens reagent

An oxidizing agent that reacts with aldehydes only; a positive test is indicated by a silver mirror ($Ag$).

Hemiacetal

A functional group consisting of a carbon atom bonded to one $OR$ group and one $OH$ group.

Acetal

A functional group consisting of a carbon atom bonded to two $OR$ groups; used to protect aldehydes and ketones.

Acetal Formation Requirements

Driven forward by using excess alcohol and the removal of water.

Aqueous acid ($H_3O^+$)

The reagent used to remove acetal protecting groups.

Raney nickel/$H_2$

Reagents used to remove thioacetals.

Primary Amine

An amine with the formula $RNH_2$.

Secondary Amine

An amine with the formula $R_2NH$.

Tertiary Amine

An amine with the formula $R_3N$.

Amine Basicity and Nucleophilicity

Amines are basic and nucleophilic because nitrogen possesses a reactive lone pair.

Imine

A product formed from the reaction of a primary amine and a carbonyl, ideally at pH $4-5$.

Enamine

A product formed from the reaction of a secondary amine and a carbonyl, ideally at pH $4-5$.

Reductive amination

A reaction sequence that results in the overall conversion of a carbonyl to an amine.

Wolff-Kishner reduction

A reaction using $NH_2NH_2$, base, and heat to convert a carbonyl to a $CH_2$ group.

Clemmensen reduction

A reaction using $Zn(Hg)$ and $HCl$ to convert a carbonyl to a $CH_2$ group.

Wittig reaction

A reaction that converts a carbonyl into an alkene using a phosphorus ylide.

1,2-addition

The type of addition performed by a Grignard reagent on a carbonyl source.

1,4-conjugate addition

The type of addition performed by a cuprate, such as a Gilman reagent ($R_2CuLi$).