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What suffix is used for naming an aldehyde?
-al
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What suffix is used for a an aldehyde attached to a ring?
-carbaldehyde
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What suffix is used for a ketone?
-one
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How are Aldehydes normally prepared?
- Oxidation of primary alcohols
- Partial reduction of esters
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How are Ketones normally prepared?
- Oxidation of secondary alcohols
- Addition of diorganocopper reagents to acid chlorides
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What is the most common reaction of aldehydes and ketones?
Nucleophilic addition reaction
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What reagents are used to reduce aldehydes and ketones?
NaBH4 or LiAlH4
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Aldehydes and ketones are reduced by NaBh4 or LiAlH4 to yield ____ and ____ alcohols respectively.
secondary, primary
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Addition of Grignard reagents to aldehydes and ketones gives ____ and ___ alcohols respectively.
tertiary, secondary
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Addition of HCN to aldehydes and ketones yields ___.
cyanohydrins
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Primary amines add to carbonyl compounds yielding ___.
imines
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Secondary amines to carbonyl compounds yield ____.
enamines
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Reaction of an aldehyde or ketone with hydrazine and base gives _____.
an alkane (wolff-kishner reaction)
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Alcohols add to carbonyl groups to yield ___ which act as ____.
acetals, protecting groups
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Phosphoranes add to aldehydes and ketones to give ___.
alkenes (Wittig reaction)
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Alpha,beta-Unsaturated aldehydes and ketones often react with nucleophiles to give the product of ____ or ___.
conjugate addition; 1,4-addition
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Alpha,beta-Unsaturated aldehydes and ketones react with a diorganocopper reagent resulting in the addition of ___, ___, or ___ to the double bond.
alkyl, aryl, or alkenyl group
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Preparation
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Oxidation
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Secondary alcohol to ketone
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Partial Reduction
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Oxidation
- Also can use KMnO4 and hot HNO3
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Aldehydes are easily oxidized to yield ___, but ketones are generally ___ toward oxidation. This is because aldehydes have a -CHO ___, while ketones do not.
- carboxylic acids, inert.
- proton
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Tollens' reagent
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Ketone Cleavage
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Formation of gemdiol by hydration occurs when an aldehyde or ketone is treated with a nucleophile H-Y, where Y is ___ and can stabilize a negative charge. Examples of Y include ____.
- electronegative
- -OH, -OR, -Cl, -Br, -HSO4(-)
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- Can do the "same" with Aldehyde and LiAlH4 (and ether solvent) to get a primary alcohol
- Not reversible
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Stoichometry
4 Ald/Ket + 1 NaBH4 (LiAlH4) ->
4 Alcohol
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Stereochemistry of Hydride attack on cyclohexal?
Equatorial favored 90% of time.
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- X: Cl, Br, I (not F)
- R'': Alkyl, vinly, aryl, alkynyl
- Incompatible with R-OH, H2O, -COOH, -NH2
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- Note: C-C bond formed
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----H3O+---->
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- Imine
- Need some acid, but not too much
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- Enamine
- Need some acid, but not too much
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Wolff-Kishner
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Addition of alcohols
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Wittig
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Alpha/Beta
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Alpha/Beta
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Alpha/Beta
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Test for Ketone
- Oxime
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Test for Acetone
- Dinitrophenylhydrazone
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Acetal Formation
- Completely reversible
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Under what conditions are ketals stable?
Neutral or basic
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How would you protect a keto group during reduction?
- Convert to acetal/ketal with 2 R-OH and HCl catalyst or diol.
- Reduce with LiAlH4.
- Remove acetal with aqueous acid.
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Cannizzaro Reaction
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Raney-Ni
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