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23 Cards in this Set

  • Front
  • Back
Aldehydes and Ketones: Nomenclature
- Aldehydes with suffix -al

- Ketones with suffix -one
Aldehydes: REMEMBER

First five Aldehydes? real names?
- Formaldehyde (Methanal)

- Acetaldehyde (Ethanal)

- Propionaldehyde (Propanal)

- Butyraldehyde (Butanal)

- Valeraldehyde (Pentanal)
Aldehydes: Nomenclature

another suffix? (when complicated molecules)

what is prefix when functional group?
- carbaldehyde

- formyl
Ketones: Nomenclature

what is name when prefix?
- oxo
Aldehydes and Ketones: Physical Properties
- high B.P.
Aldehydes and Ketones: Synthesis

3 Types
- Oxidation of Alcohols

- Ozonolysis

- Friedel-Crafts Acylation
Synthesis: Oxidation of Alcohols

which carbonyl type does it create?

- can create both aldehydes and ketones.
> Aldehyde from primary alcohol
> Ketone from secondary alcohol

- primary alcohol/secondary alcohol + PCC/CrO3 (Jones)
Synthesis: Ozonolysis of Alkenes

which carbonyl created?

- can make both aldehyde and ketone

- alkene + ozone >>> aldehyde or ketone
Synthesis: Friedel-Crafts Acylation

carbonyl type created?

- creates only Ketones

- Carbonyl halide (Cl) + benzene + AlCl2
Aldehydes and Ketones: Reactions with carbonyl substrates

5 types
- Enolization and Reactions of Enols

- Addition Reactions

- Aldol Condensation

- Wittig Reaction

- Oxidation and Reduction
Reactions: Enolization and Reactions of Enols

What is the process of Enolization?

What are the two tautomers of ketones and aldehydes?
>which form is preferred?

are tautomers resonance structures?
- The process of interconverting between keto and enol.

- the tautomers are the KETO form and the ENOL form
> the Keto- form is preferred state.

- NO, they are structural isomers.
Reactions: Enolization and Reactions of Enols

where is the Enol form important?

how to create an enol intermediate?

whats the reaction type? whats its name?

- Enols are the necessary intermediates of many ald/keto reactions.

- can use strong base (LDA or KH), creates enolate carbanion.

- carbanion reacts via Sn2 reaction, with unsaturated (alkenes present) carbonyl compounds in MICHAEL ADDITIONS
Reactions: Addition Reactions

4 types
- Hydration

- Acetal and Ketal formation

- Reaction with HCN

- Condensations with Ammonia Derivatives
Addition Reactions: General Reaction Mechanism
- Nucleophilic addition to a carbonyl
Addition Reactions: Hydration (OH)

What is the nucleophile? product?

what increases the rate?
- aldehyde/ketone + water >>> geminal diols

- adding small amount of base or acid.
Addition Reactions: Acetal and Ketal Formation

what is the nucleophile? product?
> what does one equivalent of this Nu- make?
> what does two equivalents of this Nu- make?

reaction mechanism?

whats a ketal? whats a acetal?
- ROH is nucleophile.
> aldehyde goes to hemiacetal, then acetal
> ketone goes to hemiketal, then ketal

- one equivalent makes a hemiketal or hemiacetal
- two equivalents makes a ketal or acetal.

- same as hydration, it is catalyzed by anhydrous acid.
Addition Reactions: Reaction with HCN

What is the nucleophile? product?
- the Nu- is CN-.
> Cyanohydrins are the product.
Addition Reactions:Condensations with Ammonia Deriv.'s

what is nucleophile?

simplest reaction case?
- ammonia/ammonia derivatives are Nu-.

- ammonia adds to carbon atom (double bonded to carbon). This is called an Imine.
> first part Nucleophilic addition
> second part (after tetrahedral int. formed) Nucleophilic SUBSTITUTION.
Reactions: The Aldol Reaction

nucleophile? target?

reagents? product?
- Aldehyde is both nucleophile (enol form) and target (keto form).
> base turns carbonyl group into enol form
> enables reactivity with other carbonyl groups.

- base (OH-)

- product is an ALDehyde and an alcohOL, so the compound is called an 'Aldol'
Reactions: Aldol Condensation

whats needed?

what type of reaction is this?
- a stronger base and after aldol formed, high heat.

- product is an alpha,beta-unsaturated aldehyde + water

- E1 reaction!
Reactions: The Wittig Reaction

overall reaction?
> step 1? nucleophile? Step 1a? nucleophile?
> step 2? nucleophile? what happens after binding to target?
- C=O (carbonyl) >>> C=C (alkene)
> step 1: is formation of phosphonium salt from Sn2 reaction of alkyl halide and nucleophile triphenylphosphine.
> step 1a: phosphonium salt is deprotonated by strong base, leading to ylide (C6H5)3P+---CH2-.
> step 2: ylide is a carbanion, so new nucleophile. combines with aldehyde or ketone to form BETAINE.
> Betaine forms a 4-part ring intermediate.
> this then decomposes to alkene.
Reactions: Oxidation

oxidative ranking compared to alcohols and carboxylic acids?

what do aldehydes oxidize to?
what do ketones oxidize to?
- Oxidization
> high - Carboxylic Acids>Alde/Keto>Alcohols - low

- aldehydes oxidize to carboxylic acids.
- ketones dont oxidize farther.
Reactions: Reduction

reduction to alcohols: can Alde? can Keto?
>most common reducing agents?

reduction to alkanes: can both?
> method 1: reducing reagent? restriction?
> method 2: reducing reagent?
- both Aldehydes and Ketones can reduce to Alcohols
>LAH or NaBH4

- both can reduce to alkanes
> Wolff-Kishner --- carbonyl converted to hydrazone (C=NNH2), then heated in base to form alkane. restricted to only when substrate is stable in basic conditions
> Clemmensen --- heat, Hg(Zn)/HCL, forms alkane.