Aldehydes and Ketones (Chapter 17)

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Total cards: 24•Content version: v4•Public deck•Updated: 8/1/2026

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Front (Question)

Hybridizations within Aldehyde/Ketone

Back (Answer)

• The carbon (C) is sp2-hybridized. • The oxygen (O) is sp2-hybridized.

Front (Question)

Reagents: Jones Oxidation

Back (Answer)

• NaCr2O7, H2SO4 • CrO3, H2SO4, H2O

Front (Question)

1° Alcohol → Aldehyde

Back (Answer)

PCC Pyridinium Chlorochromate Jones Oxidation of a 1° Alcohol yeilds a Carboxylic Acid.

Front (Question)

2° Alcohol → Ketone

Back (Answer)

• Jones Oxidation • PCC

Front (Question)

1° Alkyl Benzene → Ketone

Back (Answer)

Jones Oxidation

Front (Question)

Oxidation: PCC vs. Jones

Back (Answer)

Jones Oxidation requires an aqueous acid (i.e. H2O), whereas PCC involves a non-aqeuous acid.

Front (Question)

Allylic Alcohol → Aldehyde/Ketone

Back (Answer)

Oxidation via MnO2 MnO2 is a mild oxidant (i.e. it cannot oxidize non-allylic alcohols or alkenes).

Front (Question)

Product of Allylic Alcohol Oxidation

Back (Answer)

• α,β-Unsaturated Aldehyde (if 1° Alcohol) • α,β-Unsaturated Ketone (if 2°/3° Alcohol)

Front (Question)

Alkene → Aldehyde/Ketone

Back (Answer)

Ozonolysis

#10

Front (Question)

Reagents: Ozonolysis

Back (Answer)

• O3, CH2Cl2 • Zn, CH3COOH

#11

Front (Question)

Terminal Alkyne → Ketone

Back (Answer)

Hg(II)-Catalyzed Hydration Oxymercurtion Hg(II)-catalyzed hydration is a Markovnikov addition reaction.

#12

Front (Question)

Reagents: Hg(II)-Catalyzed Hydration

Back (Answer)

HgSO4, H2O, H2SO4

#13

Front (Question)

Hydration: Markovnikov vs. Anti-Markovnikov

Back (Answer)

• Markovnikov: Alcohol (—OH) adds to the most substituted carbon. • Anti-Markovnikov: Alcohol (—OH) adds to the least substituted carbon.

#14

Front (Question)

Terminal Alkyne → Aldehyde

Back (Answer)

Hydroboration-Oxidation Hydroboration-oxidation is an anti-Markovnikov addition reaction.

#15

Front (Question)

Reagents: Hydroboration-Oxidation

Back (Answer)

• BH3 • H2O2, NaOH

#16

Front (Question)

Benzene → Aldehyde/Ketone-Substituted Benzene

Back (Answer)

Friedel-Crafts Acylation

#17

Front (Question)

Reagents: Friedel-Crafts Acylation

Back (Answer)

Acyl Halide + Lewis Acid

#18

Front (Question)

Geminal Diol vs. Vicinal Diol Gem-Diol vs. Vic-Diol

Back (Answer)

• Geminal Diol: A compound containing two alcohol groups (—OH) are bonded to the same sp3-hybridized carbon atom. • Vicinal Diol: A compound containing two alcohol groups (—OH) are bonded to adjacent sp3-hybridized carbon atoms.

#19

Front (Question)

Aldehyde/Ketone → Geminal Diol

Back (Answer)

Hydration The hydration of aldehydes/ketones can be acid-catalyzed OR base-catalyzed.

#20

Front (Question)

Geminal Diol → Aldehyde/Ketone

Back (Answer)

Dehydration The hydration of aldehydes/ketones is reversible.

#21

Front (Question)

Why must the carbonyl Oxygen be protonated in acid-catalyzed nucleophilic addition? Addition to Aldehydes/Ketones

Back (Answer)

The nucleophile present under acidic conditions is too weak to add to the carbonyl Carbon without prior protonation of the carbonyl Oxygen. Protonation of the carbonyl Oxygen increases the partial-positive charge on the carbonyl Carbon, which allows the weak nucleophile to add to the Carbon.

#22

Front (Question)

Nucleophile: Hydration of Aldehyde/Ketone

Back (Answer)

• Basic Conditions: OH– • Acidic Conditions: H2O

#23

Front (Question)

Work-Up Step: Hydration of Aldehyde/Ketone

Back (Answer)

• Basic Conditions: Protonation via H2O • Acidic Conditions: Deprotonation via H2O

#24

Front (Question)

Equilibrium Preference of Aldehyde/Ketone Hydration

Back (Answer)

• Hydration of ketones will favor the reagent (i.e. Ketone) over the product (i.e. 2° Gem-Diol) • Hydration of aldehydes will favor neither the reagent (i.e. Aldehyde) nor the product (1° Gem-Diol). • Hydration of formaldehyde will favor the product (i.e. Methanediol) over the reagent (i.e. Formaldehyde). • Hydration of acyl halides will favor the product (i.e. Halide Gem-Diol) over the reagent (i.e. Acyl Halide). The alcoholic addition to aldehydes/ketones has an identical equilibrium preference trend.