Organic Chemistry 2 - Learning Objectives

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.