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Organic Chemistry 2 - Learning Objectives

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    UI Springfield CHE 269
    Organic Chemistry II
    Spring 2016: Morsch

    Homework Problems
    Homework Solutions

    Chapter 15: Radical Reactions

    • Draw initiation, propagation and termination steps for radical halogenation reactions.
    • Explain reactivity/selectivity principle applied to radical halogenation (chlorination vs. bromination).
    • Draw products for radical addition to alkenes.
    • Draw products for radical allyl addition to alkenes.

    Chapter 16: Conjugation, Resonance and Dienes

    • Explain stability of conjugated dienes using heats of hydrogenation
    • Draw resonance hybrids. 
    • Draw mechanism for 1,2 and 1,4 addition to conjugated dienes.
    • Explain kinetic vs. thermodynamic effects in reactions of conjugated dienes.
    • Draw products of Diels-Alder reactions (including stereospecificity)
    • Draw Diels-Alder mechanism.
    • Explain reactivity of dienes for Diels-Alder reactions.

    Chapter 18: Electrophilic Aromatic Substitution

    • Draw EAS mechanism: halogenation, nitration, sulfonation, FC alkylation, and FC acylation.
    • Draw mechanism for formation of electrophiles.
    • Draw mechanism for Friedel-Crafts alkylation rearrangements.
    • Explain direction effects for substituted benzenes – o,p directors and m-directors.
    • Explain activation vs. deactivation of aromatic rings based on substituents.
    • Determine products of EAS for mono-substituted aromatics.
    • Determine products of EAS for di-substituted aromatics.
    • Determine synthesis schemes for poly substituted aromatics.
    • Draw products of benzylic halogenation reactions.
    • Draw the products of oxidation and reduction reactions applied to aromatic side chains:

    Permanganate oxidation, Wolff-Kishner reduction, Clemmensen reduction, Tin reduction

    Chapter 19: Acidity of Carboxylic Acids

    • Name carboxylic acids following IUPAC.
    • Draw reactions and syntheses to form carboxylic acids.
    • Apply carboxylic acids to fatty acids and pain relief topics.
    • Determine relative acidity of carboxylic acids based on inductive effects.
    • Determine acidity based on aromatic substituents.
    • Determine structures of amino acids when neutral, acidic and basic.

    Chapter 20: Introduction to Carbonyl Chemistry

    • Explain general reactivity of carbonyl groups.
    • Draw nucleophilic addition mechanism.
    • Draw nucleophilic acyl substitution mechanism.
    • Draw mechanism and products for reduction of carbonyls with lithium aluminum hydride and diisobutyl aluminum hydride.
    • Rank reactivity of organometallic reagents copper, magnesium and lithium compounds.
    • Draw mechanisms for reaction of organometallic compounds with aldehydes and ketones.
    • Use acetals as protecting groups of aldehydes in synthesis problems.
    • Draw mechanisms for reaction of organometallic compounds with various carboxylic acid derivatives.
    • Draw products of reaction of organometallic reagents with carbon dioxide.
    • Draw mechanism for addition of organometallic compounds to a, b unsaturated carbonyl compounds.
    • Solve synthesis problems incorporating carbonyl chemistry.

    Chapter 21: Nucleophilic Addition

    • Explain relative reactivity of aldehydes and ketones.
    • Name simple aldehydes and ketones using IUPAC nomenclature.
    • Draw products of reactions that form aldehydes and ketones (previous material).
    • Draw basic (or strong nucleophile) nucleophilic addition mechanism.
    • Draw acid catalyzed nucleophilic addition mechanism.
    • Draw mechanism and products of the Wittig reaction.
    • Draw mechanism and products of nucleophilic addition of 1o and 2o amines (imine and enamine formation).
    • Draw mechanism for formation of acetals and hemi-acetals.
    • Apply hemi-acetal formation to pyranose and furanose forms of sugars.
    • Apply acetal formation as protecting groups of carbonyls in synthesis problems.

    Chapter 22: Nucleophilic Acyl Substitution

    • Name simple carboxylic acid derivatives using IUPAC nomenclature.
    • Draw generic nucleophilic acyl substitution reaction.
    • Rank leaving groups/reactivity of carboxylic acid derivatives.
    • Draw mechanisms for reaction of acid derivatives with hydride reducing agents and organometallics.
    • Draw mechanism to form acid halides from carboxylic acids.
    • Draw mechanisms to transform each carboxylic acid derivative into the less reactive derivatives.
      • acid halide to anhydride, ester, amide, carboxylic acid
      • anyhdride to ester, amide, carboxylic acid
      • carboxylic acid to amides (DCC)

    Chapter 23: Carbonyl Alpha Substitution Reactions

    • Draw general alpha carbon reaction mechanisms incorporating enols for neutral/acidic reactions and enolates for basic reactions
    • Draw basic and acidic tautomerizations.
    • Determine if a kinetic or thermodynamic enolate will form, based on reaction conditions.
    • Draw kinetic and thermodynamic enolate reaction mechanisms.
    • Draw mechanisms for halogenation at alpha carbon. 
    • Draw mechanisms for direct enolate alkylation.

    Chapter 24: Carbonyl Condensation Reactions

    • Draw aldol reaction mechanisms (Single reactant, crossed, directed, and intramolecular).
    • Draw Claisen condensation mechanism (Single reactant and Crossed)
    • Draw Intramolecular Claisen mechanism (Dieckmann cyclization).
    • Draw sulfur analogue of Claisen condensation (as in acetyl CoA).
    • Determine products of Michael type reactions.

    Chapter 25: Amines

    • Draw reactions and syntheses used to form amines (reduction of nitro, amide, nitriles; reaction with alkyl halides).
    • Determine relative basicity of amines based on availability of the lone pair electrons.

    Chapter 26: Synthetic Polymers

    • Draw addition polymerization reactions (including cationic and radical polymerization).
    • Draw condensation polymerization reactions.


    Organic Chemistry 2 - Learning Objectives is shared under a CC BY-NC-SA 4.0 license and was authored, remixed, and/or curated by LibreTexts.

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