Be able to picture the means by which acid catalysis activates the hydroxyl group as a leaving group, enabling alcohols to undergo SN1 Substitution or E1 Elimination.

Remember that Thionyl Chloride and Phosphorus Tribromide enable the transformation of an alcohol into an alkyl halide.

Be able to assign oxidation number to the hydroxyl carbon of an alcohol and be able to place alcohols within the redox sequence including aldehydes/ketones and carboxylic acids.

Understand the acid-base properties of alcohols and the significance within reaction chemistry, i.e. the use of alkoxide anion as a nucleophile.

Recall how ethers may be formed as well as characterize their reactivity.

Be capable of elucidating the nature of epoxides, their formation and basic reactivity.

Aldehydes and Ketones

Be capable of characterizing the two major classes of aldehyde-ketone reactions, those involving nucleophilic attack on the carbonyl carbon and those occuring by means of keto-enol tautomerism.

Although you don't need to worry about every proton movement, you should be able to reproduce the decisive phases of Acetal Formation, Reductive Amination, and Reaction of Aldehydes and Ketones with Grignard Reagents.

Be able to recognize and characterize these other reactions involving nucleophilic attack on a carbonyl carbon if they are presented to you: The Wittig Reaction, The Wolff-Kishner Reaction and The Cannizzaro Reaction.

Recognize an enol. Be comfortable reproducing acid or base catalyzing enolization on paper.

Understand what it means to say that Aldol Condensation involves both keto-enol tautomerism and nucleophilic attack on the carbonyl carbon. Know this reaction backwards and forwards.

Be able to predict the product from the reagents for Alpha Halogenation, Haloform Reaction, as well as Conjugate Nucleophilic Addition. Have a good sense of these mechanisms.

Understand the place of aldehydes and ketones in the redox sequence with alcohols and carboxylic acids.

Carboxylic Acids and Derivatives

Understand how resonance stabilization of the carboxylate anion promotes the acidity of carboxylic acids.

Understand the order of stability among carboxylic acid derivatives.

See nucleophilic acyl substitution mechanisms as recapitulations of a general mechanism involving formation and resolution of a tetrahedral intermediate: Acid Halide Formation, Fischer Esterification, Use of Carboxylate Anion Nucleophile to form Esters, Hydrolysis of Acid Halides, Reaction of Acyl Halide with Ammonia or Amine, Esterification of Acid Halides, Esterification of Acid Anhydrides, Saponification of Esters. Acyl substitution appears on many MCATs.

Understand the role acid catalysis plays in facilitating some acyl substitution mechanisms.

Be able to recognize and follow Claisen Condensation, Nitrile Hydrolysis, Nitrile Reduction or Hofmann Rearrangement if you were presented with the mechanism.


Understand the properties of amines as weak bases.

Be familiar with Amine mechanisms we have seen in other contexts including SN1 or SN2 Substitution with Alkyl Halides where an Amine is the nucleophile, the reaction of Amines as the nucleophile with Aldehydes and Ketones such as occurs in Reductive Amination, the the reaction of Amines with Carboxylic Acid Derivatives such as with Acyl Halides and in Hofmann Elimination.

Organic Phosphorus Compounds

Be familiar with the structural formulas and nomenclature for the range of oxidation states of organic phosphorus compounds from phosphines to phosphate esters.

Be able to picture the deprotonation states at physiological pH of phosphoric acid species and organic mono-, di-, and tri-phosphates.

Be able to picture the general mechanism of phosphoryl transfer reactions and understand their transcendent importance in biochemistry.

Understand the mechanism of the phosphorylation of glucose by ATP and appreciate its importance as a critical metabolic step.

Understand the structure of a phosphorus ylide, such as plays a role in the Wittig Reaction.

Organic Sulfur Compounds

Understand the structural formulas and nomenclature for the range of oxidation states of organic sulfur compounds from thiols and sulfides to sulfate esters.

Be familiar with the use of thiol compounds as nucleophiles especially in the context of the biochemistry of cysteine side-chains.

Understand the mechanism by which two cysteine side chains can covalently interact in a protein to produce a disulfide.

Bird's Eye View

Knowledge Mapping

Psychology & Sociology

Critical Analysis and Reasoning

Improve the stamina of your reading attention. Practice sustaining your focus through dense reading material.

Understand the intentions of the writers of Verbal Reasoning questions on the MCAT.