UGA CHEM2212 Lab Practical Spring 2026

Carvone to carvacrol starting material

(R)-(-) carvone

Carvone to carvacrol catalyst/solvent

6M H₂SO₄

Carvone to carvacrol product

carvacrol

What is the name of the process in carvone to carvacrol?

Acid-catalyzed elimination

Why is carvone to carvacrol thermodynamically favorable?

Aromaticity

Carvone to carvacrol mechanism steps

acid-catalyzed tautomerization → carbocation rearrangement → elimination

Carvone to carvacrol monitoring

reflux

Carvone to carvacrol first extraction solvent

diethyl ether

Carvone to carvacrol basification solvent

NaHCO₃ sodium bicarbonate FORMS CO₂ GAS!!

Carvone to carvacrol drying agent

Na₂SO₄ sodium sulfate

Carvone to carvacrol: Could you have substituted (R)-carvone for its enantiomer in this reaction?

Yes, (S)-carvone could have been used since the reaction produces an achiral product at the end. Chirality is lost after the 1,2-hydride shift because a carbocation is sp2-hybridized

Reduction of unknown A/K starting material

Unknown A/K

Reduction of unknown A/K reducing agent

NaBH₄ sodium borohydride

Reduction of unknown A/K solvent

EtOH ethanol

Reduction of unknown A/K product

1* or 2* alcohol

Reduction of unknown A/K: what can/can’t NaBH₄ reduce?

Reduces: aldehydes & ketones
Doesn’t reduce: esters, amides, carbox acids

Reduction of unknown A/K nucleophile

NaBH₄ sodium borohydride

Reduction of unknown A/K monitoring

microwave reflux

Reduction of unknown A/K isolation method

L/L extraction

Reduction of unknown A/K drying agent

Magnesium sulfate

Reduction of unknown A/K: how do impurities impact melting point?

Broaden and depress

Reduction of unknown A/K: Would ethyl acetate (EtOAc) be a good solvent for this reaction?

Ethyl acetate would be a suitable solvent for the reaction because sodium borohydride is not strong enough to reduce an ester

Oxidation of unknown alcohol starting material

Unknown alcohol (2-pentanol, 3-pentanol, 3-methyl-2-butanol)

Oxidation of unknown alcohol oxidizing agent

NaOCl sodium hypochlorite (bleach), specifically HOCl hypochlorous acid

Oxidation of unknown alcohol solvent

CH₃CO₂H acetic acid

Oxidation of unknown alcohol product

Ketone (2-pentanone, 3-pentanone, 2-methyl-2-butanone)

Oxidation of unknown alcohol monitoring

KI paper (blue = xs bleach, continue with quenching)

Oxidation of unknown alcohol quenching agent

NaHSO₄ sodium bisulfate

Oxidation of unknown alcohol: what does sodium bisulfate quench?

excess hypochlorite

Oxidation of unknown alcohol basification agent

6M NaOH sodium hydroxide (neutralized residual acetic acid)

Oxidation of unknown alcohol: purpose of basification?

neutralize residual acetic acid allowing it to be water-soluble while the product remained un-ionized

Oxidation of unknown alcohol drying agent

MgSO₄ magnesium sulfate

Oxidation of unknown alcohol: What reactive intermediate is formed in situ?

HOCl hypochlorous acid is formed. NaOCl reacts with acetic acid to form hypochlorous acid (HOCl), which then reacts with the alcohol to form the ketone/aldehyde.

Oxidation of unknown alcohol: What is the purpose of a base wash?

Sodium hydroxide (NaOH) was used to convert acetic acid (CH3COOH) into sodium acetate (Na+CH3COO-) which is water-soluble

Oxidation of unknown alcohol: wash vs extraction?

Wash = removes impurities

Extraction = moves desired product from one layer to another

Diels-Alder starting materials

cyclopentadiene, unknown alkyne dienophile

Diels-Alder product

bicyclic D-A product

Diels-Alder monitoring

microwave distillation to crack dicyclopentadiene

Diels-Alder: what makes a good diene?

electron-rich, conjugated double bonds, s-cis conformation

Diels-Alder: what makes a good dienophile?

electron-poor

FC alkylation starting materials

1,4-dimethoxybenzene, 2 eq unknown 3* alcohol

FC alkylation solvent

CH₃CO₂H acetic acid

FC alkylation cataylst

H₂SO₄ sulfuric acid

FC alkylation reaction type

EAS

FC alkylation: what makes EAS reactions proceed faster?

strong EDG on ring

FC alkylation electrophile

in situ from 3* and H₂SO₄

FC alkylation monitoring

In chilled EM flask, reacted at room temp

FC alkylation quencher

ice cold water, white precipitate

FC alkylation recrystallization solvent

MeOH methanol

Wittig starting materials

benzene ylide, 9-anthranaldehyde

Wittig reagent

NaOH sodium hydroxide

Wittig product

you know what it looks like and im not writing that name

Wittig reaction mixture details

non-homogenous (ylide = hydrophilic, aldehyde = hydrophobic)

Wittig: what alkyl halides are best for making ylides?

Primary alkyl halides (S_N2 rxn)

Wittig mechanism

NaOH added dropwise while stirring

Wittig isolation

L/L extractionW

Wittig drying agent

CaCl₂ calcium chloride

Wittig: What reactive intermediate is formed in situ?

ylide

Wittig: What kind of alkene stereochemistry is preferred?

E-isomers

Wittig: What is the driving force behind the reaction?

Generation of triphenylphosphine oxide is preferred because the P—O bond is very strong

Fischer esterfication starting materials

Acetic acid, unknown 1* alcohol (1-propanol, 1-butanol, isopentanol)

Fischer esterfication catalyst

H₂SO₄ sulfuric acid

Fischer esterfication solvent

CH₃CO₂H acetic acid

Fischer esterfication product

ester

Fischer esterfication mechanism

MICROSCALE REVERSIBILITY

Fischer esterfication: what drives the equilibrium towards products?

Le Chatelier’s principle: excess carboxylic acid

Fischer esterfication basification

NaHCO₃ sodium bicarbonate CO2 GAS!!

Fischer esterfication drying agent

Na₂SO₄ sodium sulfate

Fischer esterfication: What is the purpose of heating the reaction in the microwave?

Microwaves are absorbed by polar substances like water and alcohols, and the molecules begin to vibrate and produce heat very quickly. The heat is used to shift the equilibrium toward the products and speed up the reaction

Fischer esterfication: How were Le Châtelier’s principles employed in this reaction? Why were they necessary?

• Esterification is in equilibrium, ∴ conditions are needed to push equilibrium toward products

• An excess of acetic acid is used to shift the equilibrium

• Removal of water can also shift equilibrium toward the products

Amide synth starting materials

acetic anhydride, unknown 1* amine

Amide synth catalyst

Al₂O₃ aluminum oxide

Amide synth solvent

(CH₃CO)₂O acetic anhydride

Amide synth products

amide, acetate

Amide synth: endo or exo?

exothermic

Amide synth: how does the catalyst (Al₃O₂) work?

Provides basic polar surface for the reaction to take place on & neutralizes acetic acid byproduct as it forms

Amide synth extraction

ethyl acetate

Amide synth: why was ethyl acetate used to extract?

unknown amide and Al₃O₂ are insoluble

Amide synth separation method

Gravity filtration

Amide synth: Why is it essential that no water or alcohols are present in the reaction?

Alcohols and water will quench the reaction by reacting with acetic anhydride

Aldol nucleophile

acetone

Aldol electrophile

unknown aldehyde

Aldol solvent

EtOH ethanol

Aldol catalyst

NaOH sodium hydroxide

Aldol favored product

alpha, beta-unsaturated ketone (favored bc of conjugation)

Aldol: Why is o-anisaldehyde incapable of undergoing an aldol reaction with itself?

Anisaldehyde does not have an alpha proton and thus cannot form an enolate to undergo an aldol reaction

Aldol: What were to happen if you added NaOH to your reaction vessel first, then added acetone?

Acetone will form an enolate first, which can then react with another molecule of acetone to form the self-aldol product