MCAT Organic Chemistry Mechanisms Summary

Gold Standard MCAT Organic Chemistry Mechanisms and Reactions ('cheat sheet' notes)

Carboxylic Acids | Aldehydes & Ketones | Reaction List | IR Spec

Conquer MCAT Organic Chemistry Reactions with our high-yield Mechanisms Summary! This page highlights the most frequently tested key reaction mechanisms and concepts. By grounding your review in basics like electrostatics (opposites attract), you will successfully minimize memorization and master complex reaction pathways. Ready to test your knowledge? Check out the full topic list or access targeted Organic Chemistry practice questions in our free MCAT practice test today!

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Carboxylic Acid Synthesis and Nucleophilic Acyl Substitution

Reactions of Aldehydes and Ketones: Nucleophilic Addition

Common Organic Chemistry Reactions 23-31

High-Yield MCAT Organic Chemistry Reactions List

Most reactions presented can be derived from basic principles (i.e. ORG 1.6, 7. 1). Many of the reactions are cross-referenced for further information.

An acid chloride reacts with a Grignard reagent to produce a tertiary alcohol. See ORG 1.6, 9.1.
An acid chloride reacts with a primary or secondary amine to produce an amide. See ORG 9.3 & 11.2.
A carboxylic acid reacts with SOCl₂ or PCl₅ to produce an acid chloride. See ORG 9.1
An acid chloride reacts with an alcohol (e.g. ethanol) to produce an ester. See ORG 9.4.
An amide reacts with LiAlH₄ to produce an amine. See ORG 8.2, 9.3.
A carboxylic acid reacts with an alcohol (e.g. ethanol) to produce an ester. See ORG 8.2.
An ester reacts with LiAlH₄ to produce a primary alcohol. See ORG 8.2, 9.4.
A carboxylic acid reacts with base to produce a carboxylate anion. See CHM 6.3 & ORG 8.1.
An ester reacts with a Grignard reagent to produce a tertiary alcohol. See ORG 1.6, 8.1.1, 9.4.
A Grignard reagent reacts with carbon dioxide to produce a carboxylic acid. See ORG 8.1.1.
A nitrile reacts with aqueous acid to produce a carboxylic acid. See ORG 8.1.1.
A carboxylate ion reacts with ethyl iodide to produce an ester.
An alkyl halide reacts with Mg/ether to produce a Grignard reagent.
An alkyl halide reacts with NaCN to produce a nitrile. See ORG 6.2.3.
A nitrile reacts with LiAlH₄ to produce an amine. See ORG 8.2.
A primary alcohol reacts with HBr to produce an alkyl halide.
An acid chloride reacts with NaBH₄ to produce a primary alcohol. See ORG 8.2, 9.1.
A primary alcohol reacts with CrO₃/pyridine to produce an aldehyde. See ORG 6.2.2, 7.2.1.
A acid chloride reacts with H₂/Pd/C to produce an aldehyde. See ORG 7.1, 7.2.1, 9.1.
An aldehyde reacts with NaBH₄ to produce a primary or secondary alcohol. See ORG 7.1, 8.2.
An aldehyde reacts with KMnO₄ to produce a carboxylic acid. See ORG 7.2.1, 8.1.1.
A carboxylic acid reacts with LiAlH₄ to produce a primary alcohol. See ORG 8.2.
An imine reacts with NaBH₄ to produce a secondary amine. See 7.2.3, 8.2.
An aldehyde reacts with a primary amine to produce an imine. See ORG 7.2.3.
An aldehyde reacts with a Grignard reagent and ether to produce a secondary alcohol. See ORG 1.6, 7.1.
An aldehyde reacts with aqueous NaCN. See ORG 7.1.
A secondary alcohol reacts with Na₂CrO₇ or CrO₃/pyridine to produce a ketone. See ORG 6.2.2.
A ketone reacts with NaBH₄ to produce a secondary alcohol. See ORG 7.2.1.
An acetal reacts with aqueous acid to produce an aldehyde. See ORG 7.2.1/2.
An aldehyde reacts with an alcohol (e.g. ethanol) and acid to produce an acetal. Note that using with less EtOH/H⁺, a hemiacetal will form. See ORG 7.2.2.
A ketone reacts with a Grignard reagent to produce a tertiary alcohol. See ORG 1.6, 9.

IR Spectroscopy

Memorize at least the following IR spectra data for the MCAT:

Approx. 3300 cm^-1 for -OH (alcohol functional group)
Approx. 1700 cm^-1 for C=O (carbonyl functional group)

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