Properties of Various Groups as Relevant to the MCAT

    Group

    Elimination
    reactions

    Addition
    reactions
    Substitution
    reactions
    Acidity/
    Basicity
    Solubilty in water*

    C-H

    Free radical;
    electrophilic aromatic if part of benzene ring

    Generally
    neutral

    Poor

    Carbon-carbon double bond
    C=C

    Electrophilic

    Generally
    neutral

    Poor

    Hydroxyl
    -OH

    Dehydration

    Nucleophilic

    Very weak acid

    Good

    Carbonyl
    C=O

    Nucleophilic
    (e.g. aldol condensation)

    Very weak acid
    a -H acidic ® carbanion

    Good

    Carboxylic acid
    -COOH

    Nucleophilic
    (can form esters, acid chlorides, anhydrides, amides, keto acids)

    Weak acid

    Good

    -Halide

    Nucleophilic

    Generally
    neutral

    Poor

    Benzene

    Electrophilic aromatic

    Generally
    neutral

    Poor

    Ether
    C-O-C

    The acid cleavage of ethers involves a nucleophilic substitutionVery weak base

    Good

    Phenol

    -H attached to benzene ring: Electrophilic aromatic

    Weak acid

    Good

    Amine
    - NH2

    Amine acts as a nucleophile in SN2 reaction with acid chloride to form an amide; similar reaction with alkyl halides to form alkylamines

    Weak base

    Good

    * Generally, a compound is water-soluble if it has only one to three carbon atoms and a hydrophilic group, especially one that can form hydrogen bonds with water molecules.

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