Chemistry 3720: Aldehydes and ketones
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Which statement is not true of a tertiary alcohol?
1. Reacts with NaH
2. OH ~3400 cm-1 IR
3. Oxidized by PCC
4. Has pkA of ~16-18
5. Reacts with HBr
Not oxidized by PCC
When a primary alcohol is oxidized with PCC, what type of molecule is formed?
Reduction of a ketone with NaBH4 results in what type of product?
A secondary alcohol
Methylphenyl ketone will not react with which of the following?
1. NaBH4 in CH3OH
2. Excess CH3OH/cat. H+
3. NaCN in HCl
4. Excess NaOH/I2
5. PCC or PDC
The ketone will not be oxidized by PCC or PDC
Reaction of an aldehyde with RLi, followed by an acid quench, results in what type of alcohol product?
A secondary alcohol
Which reagent is used to oxidize primary alcohols to carboxylic acids; PCC, Na2Cr2O7/H2SO4, or LiAlH4?
Which solvent must not be used with RLi or RMgBr reagents in addition to aldehydes or ketones; THF, ether, or CH3OH?
CH3OH (it has an acidic proton)
Reaction of a ketone with excess of an alcohol and a catalytic amount of acid gives what product?
What reagent is used to oxidize a ketone to an ester?
1. PCC or PDC
2. conc. H2SO4
4. NaBH4 in CH3OH
5. NaIO4 in H2O
Which of the following molecules is not a ketone?
What type of compound is formed during the oxidation of a primary alcohol to a carboxylic acid using Na2Cr2O7/H2SO4?
1. An acetal
2. A ketone
3. A carboxylic acid
4. A hydrate
5. An ester
Which of the following is not characteristic of a typical ketone?
1. 13C signal at 200 ppm
2. IR signal at 1700 cm-1
3. Reaction with primary amine
4. Prefers enol form
5. Reaction with RMgBr
Most ketones do not prefer the enol form
Which of the following do not react with RMgBr?
4. Carboxylic acids
Which of the following could be used to conclusively distinguish propanone from propanal?
1. Iodoform test
2. IR spectroscopy
3. 13C NMR spectroscopy
4. 1H NMR spectroscopy
5. Reaction with Na2Cr2O7/H2SO4
Iodoform test (methyl ketone), 1H NMR (9 ppm for aldehyde), oxidation with Na2Cr2O7/H2SO4 (aldehyde yes, ketone no)
Which one of the following could not yield a primary alcohol?
1. Reduction of an aldehyde
2. Reduction of a carboxylic acid
3. Reduction of a ketone
Reduction of a ketone (gives secondary alcohol)
Which reactions below result in an aldehyde product?
1. Secondary alcohol with PCC
2. Primary alcohol with PDC
3. Primary alcohol with chromic acid
4. Carboxylic acid with LiAlH4
5. Ketone with NaBH4 in CH3OH
Primary alcohol + PDC produces an aldehyde
Which methods below would not push an equilibrium from ketone to acetal?
1. Add an excess of the alcohol
2. Remove the water produced
3. Distill off the acetal product
4. Use water as the solvent
5. Distill away the ketone
Using water as the solvent and distilling away the ketone would not push the equilibrium to product
Which of the following is the best reagent for turning primary alcohols into aldehydes?
1. OsO4 with H2O2
2. NaIO4 in water
3. PCC in CH2Cl2
5. H2O2 in water
PCC in CH2Cl2
Enolization of aldehydes and ketones is catalyzed by which of the following?
Acid and base would catalyze enolization
Which would be the best technique to tell an aldehyde apart from a ketone?
1. Infra-red spectroscopy
2. 13C NMR spectroscopy
3. 1H NMR spectroscopy
4. Mass spectrometry
5. Boiling point analysis
1H NMR spectroscopy would show a distinctive signal at 9 ppm for the aldehyde
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