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23 Cards in this Set
- Front
- Back
Aldehydes and Ketones: Nomenclature
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- Aldehydes with suffix -al
- Ketones with suffix -one |
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Aldehydes: REMEMBER
First five Aldehydes? real names? |
- Formaldehyde (Methanal)
- Acetaldehyde (Ethanal) - Propionaldehyde (Propanal) - Butyraldehyde (Butanal) - Valeraldehyde (Pentanal) |
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Aldehydes: Nomenclature
another suffix? (when complicated molecules) what is prefix when functional group? |
- carbaldehyde
- formyl |
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Ketones: Nomenclature
what is name when prefix? |
- oxo
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Aldehydes and Ketones: Physical Properties
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- high B.P.
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Aldehydes and Ketones: Synthesis
3 Types |
- Oxidation of Alcohols
- Ozonolysis - Friedel-Crafts Acylation |
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Synthesis: Oxidation of Alcohols
which carbonyl type does it create? reagents? |
- can create both aldehydes and ketones.
> Aldehyde from primary alcohol > Ketone from secondary alcohol - primary alcohol/secondary alcohol + PCC/CrO3 (Jones) |
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Synthesis: Ozonolysis of Alkenes
which carbonyl created? reagents? |
- can make both aldehyde and ketone
- alkene + ozone >>> aldehyde or ketone |
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Synthesis: Friedel-Crafts Acylation
carbonyl type created? reagents? |
- creates only Ketones
- Carbonyl halide (Cl) + benzene + AlCl2 |
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Aldehydes and Ketones: Reactions with carbonyl substrates
5 types |
- Enolization and Reactions of Enols
- Addition Reactions - Aldol Condensation - Wittig Reaction - Oxidation and Reduction |
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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. |
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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? reagents? |
- 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 |
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Reactions: Addition Reactions
4 types |
- Hydration
- Acetal and Ketal formation - Reaction with HCN - Condensations with Ammonia Derivatives |
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Addition Reactions: General Reaction Mechanism
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- Nucleophilic addition to a carbonyl
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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. |
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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. |
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Addition Reactions: Reaction with HCN
What is the nucleophile? product? |
- the Nu- is CN-.
> Cyanohydrins are the product. |
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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. |
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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' |
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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! |
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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. |
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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. |
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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. |