The student will be able to:

1. Expand knowledge of functional group chemistry to include ketones and aldehydes, carboxylic acids and their derivatives, and amines with an emphasis on reaction mechanisms.
2. Apply knowledge of functional groups to the chemistry of bioactive molecules, including carbohydrates and proteins.
3. Apply theoretical models that address the structure-reactivity relationships of organic compounds.
4. Design the multi-step synthesis of an expanded array of target organic molecules from simple precursors using strategies that incorporate chemo-, regio-, and stereoselectivity in the preparation of polyfunctional compounds.
5. Devise the structure of an organic compound from a combination of chemical and/or spectroscopic information.
6. Communicate effectively using the language of organic chemistry.
7. Work constructively and collaboratively in groups.

1. Expand knowledge of functional group chemistry to include ketones and aldehydes, carboxylic acids and their derivatives, and amines with an emphasis on reaction mechanisms
   1. Aromatic compounds
      1. Electrophilic aromatic substitution: mechanism, limitations, and regioselectivity
         1. Nitration
         2. Sufonation
         3. Halogenation
         4. Friedel-Crafts alkylation and acylation
      2. Nucleophilic aromatic substitution mechanism and limitations
      3. Synthesis of poly-substituted aromatics
      4. Multistep synthesis strategies
   2. Carboxylic acids
      1. Relative acidity of substituted carboxylic acids
      2. Preparation
         1. Oxidation of alcohols or aldehydes
         2. Oxidation of benzylic carbon
         3. Hydrolysis of nitriles under acidic and basic conditions
         4. Grignard reaction with alkyl, vinyl or aryl halides and CO2
      3. Reactivity (including partial or complete mechanism)
         1. Thionyl chloride and phosphorous tribromide to form acid halides
         2. Carboxylic acid chlorides to form anhydrides
         3. With alcohols and catalytic mineral acids to form esters
         4. With amines to form amides
         5. With LiAlH4 to form alcohols
         6. With molecular bromine and PBr3 then water to form alpha-brominated acids
   3. Carboxylic acid derivatives
      1. Relative reactivity of acid chlorides, anhydrides, esters, carboxylic acids, and amides: correlation to leaving group ability
      2. Interconversion of derivatives via addition-elimination mechanism
      3. Acid chloride reactivity (including partial or complete mechanism)
         1. Reduction of acid chlorides with lithium tri(tert-butoxy)aluminum hydride to form aldehydes
         2. Reaction of acid chlorides with organocuprates to form ketones
         3. Interconversion to anhydrides, esters, carboxylic acids, and amides via addition-elimination mechanism
   4. Ester reactivity
      1. Interconversion with other RC(O)LG
      2. Reduction with LiAlH4 and DIBAL
      3. Reaction with Grignard and Organolithium reagents
   5. Amide reactivity
      1. Hofmann rearrangement of amides with halogens in aqueous base
      2. Reduction with LiAlH4 and DIBAL
      3. Hydrolysis with acid or base catalyst
   6. Nitrile reactivity
      1. Hydrolysis to amides and carboxylic acids
      2. Reaction with Grignard reagents to form ketones
      3. Reaction with LiAlH4 and DIBAL to form amines and aldehydes, respectively
   7. Enolates
      1. Acidity and formation
      2. Reaction with LDA under kinetic vs. thermodynamic control
      3. α-alkylation
      4. α-halogenation under basic and acidic conditions
      5. The haloform reaction
      6. The aldol reaction
      7. Claisen condensation
      8. Mixed and directed Aldol/Claisen reactions
      9. The acetoacetic ester and malonic ester reaction sequences
      10. Decarboxylation of β-ketoacids
      11. Stabilized enolates as nucleophiles
          1. 1,3-dicarbonyl compounds
          2. Enamines
   8. Amines
      1. Properties
      2. Preparation
         1. From other amines via nucleophilic substitution
         2. From nitriles, amides and azides via reduction
         3. Gabriel synthesis
         4. From aldehydes and ketones via reductive amination
      3. Reactivity (including partial or complete mechanism)
         1. Hofmann elimination
         2. Mannich reaction
         3. Nitrosation and diazotization of amines
         4. Reactions of aryldiazonium ions
         5. Reactivity of phenols
2. Apply knowledge of functional groups to the chemistry of bioactive molecules including carbohydrates and proteins
   1. Monosaccharides
      1. Fischer projections and D,L-nomenclature
      2. Cyclic forms and mutarotation
      3. Optical activity and structure determination
      4. Reaction with Fehling's and Tollen's solutions
      5. Condensation with amine derivatives
      6. Esterification and alkylation of hydroxy groups
      7. Formation of glycosides
      8. Sugar chain extension by cyanohydrin formation and reduction
      9. Sugar chain shortening by Ruff or Wohl degradation
      10. Disaccharides: formation and hydrolysis
   2. Amino acids and peptides
      1. Structure
      2. Acid/base properties
      3. Synthesis of amino acids
         1. SN2 reaction of ammonia with α-haloacid
         2. Diethyl acetamidomalonate alkylation, hydrolysis and decarboxylation
         3. The Strecker synthesis
      4. Peptides: primary structure and sequencing
      5. Synthesis of dipeptides using protecting groups
      6. Edman degradation
3. Apply theoretical models that address the structure-reactivity relationships of organic compounds
   1. Kinetic vs. thermodynamic control in enolate formation and α,β-unsaturated ketone addition
   2. Relative reactivity of carboxylic acid derivatives and transition state theory
   3. Proposing mechanism of unknown reactions by analogy to defined systems
   4. Assessing conformation-dependent structural features to predict reactivity
4. Design the multi-step synthesis of an expanded array of target organic molecules from simple precursors using strategies that incorporate chemo-, regio-, and stereoselectivity in the preparation of polyfunctional compounds
   1. Polysubstituted aromatics
   2. Amino acids and dipeptides
   3. Selective reactions of β-dicarbonyl derivatives
   4. Ketones and esters via enolate chemistry sequences
   5. Comprehensive functional group transformations: interconversion of all functional group categories discussed throughout the 12ABC sequence
5. Devise the structure of an organic compound from a combination of chemical and/or spectroscopic information
6. Communicate effectively using the language of organic chemistry
   1. Explain the rationale behind a chemical trend both verbally and in writing
   2. Correlate chemical structures with their nomenclature
7. Work constructively and collaboratively in groups

Not applicable.

Formative assignments and/or quizzes
Written short answer examinations
Final cumulative examination: short answer and multiple choice

Lecture
Discussion
Group work involving collaborative discussion and problem solving
Applications that exemplify scientific contributions from diverse scholars

Klein, D.. Organic Chemistry, 4th ed.. 2020.

Wade, L.G.. Organic Chemistry, 9th ed.. 2020.

Smith, Janice. Organic Chemistry, 7th ed.. 2024.

1. Short-essay questions that require synthesis and evaluation of concepts in application to real world problems.
2. Weekly reading assignments from the textbook discussing the principles that govern organic reactions (e.g., electron flow, structure/reactivity relationship, etc.).
3. Homework problems that require written explanations of chemical behavior based on application of known theoretical models.