The student will be able to:

1. Expand study of functional groups to include the chemical reactivity of alkynes, alcohols and thiols, ethers and thioethers, ketones and aldehydes, dienes, and aromatic compounds.
2. Apply theoretical models that address the structure-reactivity relationships of organic compounds.
3. Gain further proficiency in proposing a detailed mechanism of a chemical transformation in organic chemistry.
4. Design multi-step syntheses of organic target molecules from simple precursors.
5. Elucidate structures of organic molecules from spectroscopic data.
6. Communicate effectively using the language of organic chemistry.
7. Work constructively and collaboratively in groups.

1. Expand study of functional groups to include the chemical reactivity of alkynes, alcohols and thiols, ethers and thioethers, dienes, and aromatic compounds
   1. Alkynes
      1. Preparation from dihalides via double elimination
      2. Reactivity of alkynes
         1. Acidity
         2. Reaction of alkynyl anions with alkyl halides and epoxides
         3. Hydrogenation to alkanes with Pd, Pt, Ni or Rh; to cis alkenes with Lindlar catalyst; to trans alkenes with sodium in liquid ammonia
         4. Formation of Markovnikov ketone via reaction with water under acidic conditions with or without mercury (II) catalyst
         5. Formation of aldehyde or ketone via hydroboration-oxidation
         6. Reaction with molecular halogens to form di- or tetra-halides
         7. Reaction with HX to make geminal dihalides
   2. Alcohols and thiols
      1. Structure and physical properties of alcohols and thiols
      2. Reactivity of alcohols as weak acids or bases
      3. Alcohols as electrophiles in reaction with hydrogen halides, PX3, SOCl2, and POCl3
      4. Conversion to alkylsulfonates for reaction with anionic nucleophiles
      5. Rearrangement of carbocations from alcohols in strong acid
      6. Hyperconjugation and carbocation stability
      7. Oxidation of alcohols with Cr(VI): chromic acid versus PCC
      8. Thiols as Brønsted acids and as nucleophiles
      9. Formation of alcohols, ethers, and thiols from nucleophilic substitution reactions
   3. Ethers and epoxides
      1. Structure and physical properties of ethers and epoxides
      2. Reactivity of ethers as electrophiles in reaction with hydrogen halides or other strong acids in water
      3. Reactivity of epoxides as electrophiles in reaction with nucleophiles
      4. Under acidic conditions with regioselectivity at more substituted carbon (HX, H3O+, ROH under acidic conditions)
      5. Under basic conditions with regioselectivity at less substituted carbon (Nuc:-, LiAlH4)
   4. Ketones and aldehydes
      1. Relative electrophilicity
      2. Reaction with nitrogen and oxygen nucleophiles
         1. Imine and enamine formation
         2. Hydrate formation
         3. Hemiacetal and acetal formation
      3. Reaction with carbon nucleophiles
         1. Wittig reaction
         2. Grignard and organolithium reactions
      4. Carbonyl reduction and deoxygenation
         1. Hydride reducing agents LiAlH4 and NaBH4
         2. Clemmenson reduction
         3. Wolff-Kishner reduction
   5. Dienes and other delocalized pi systems
      1. Relative stability
      2. Acidity
      3. Polar addition of HX, H3O+ or X2; regioselectivity dependence on reaction conditions
      4. The Diels-Alder reaction
      5. Polymerization of conjugated dienes
   6. Benzene and aromaticity
      1. Predicting aromaticity, non-aromaticity, and anti-aromaticity
      2. Frost circles
      3. Benzylic oxidation
2. Apply theoretical models that address the structure-reactivity relationships of organic compounds
   1. Kinetic vs. thermodynamic control in addition of electrophiles to conjugated dienes
   2. Pi molecular orbitals and molecular orbital energy diagrams of pi systems in conjugated acyclic and cyclic polyenes
   3. Stereo- and regioselectivity in the Diels-Alder reaction: endo vs. exo adducts
   4. Predicting aromaticity and anti-aromaticity from molecular orbital energy diagrams
   5. Apply Hammond's postulate to predict the relative selectivity of a reaction under kinetic control as applied to free-radical reaction and diene addition reactions
3. Gain further proficiency in proposing the detailed mechanism of a chemical transformation in organic chemistry
4. Design multi-step syntheses of organic target molecules from simple precursors
   1. Recognize incompatible functional groups and use protecting group chemistry as appropriate
   2. Assess the advantages and disadvantages of alternative strategies in the synthesis of an organic target compound
   3. Apply knowledge of chemo- and regioselectivity in developing a strategy for multi-step synthesis
5. Elucidate structures of organic molecules from spectroscopic data
   1. Apply knowledge of spectroscopic methods learned in corequisite laboratory course to deduce structural information about an organic compound
      1. 1H and 13C NMR
      2. IR
   2. UV-Vis spectroscopy
      1. Electronic energy levels and absorption of UV-Vis electromagnetic radiation
      2. Color and extended conjugation
6. Communicate effectively using the language of organic chemistry
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 text and/or other peer-reviewed primary or secondary sources that require both comprehension and critical review.
3. Practice and organization of chemical reactions including drawing reaction mechanisms.