Course Outline for Chemistry 12B
Organic Chemistry II

Effective: Fall 2016
SLO Rev: 01/24/2017
Catalog Description:

CHEM 12B - Organic Chemistry II

5.00 Units

Continuation of Chemistry 12A with an introduction to the chemistry of dienes, aromatics, amines, carbanions, carboxylic acids, carboxylic acid derivatives, aldehydes, ketones and biochemical topics focusing on structure, synthesis, and mechanisms of reaction. Laboratory work in basic techniques, synthetic methods, qualitative, spectroscopic, and chromatographic analysis techniques. Chemistry 12B is the second semester in a year course in Organic Chemistry designed for students majoring in Chemistry related disciplines.
Prerequisite: CHEM 12A.
1905.00 - Chemistry, General
Letter Grade Only
Type Units Inside of Class Hours Outside of Class Hours Total Student Learning Hours
Lecture 3.00 54.00 108.00 162.00
Laboratory 2.00 108.00 0.00 108.00
Total 5.00 162.00 108.00 270.00
Measurable Objectives:
Upon completion of this course, the student should be able to:
  1. propose reasonable syntheses for compounds in the classes studied;
  2. use infrared, 1H and 13C nuclear magnetic resonance spectroscopic information and data concerning reactions or physical properties to elucidate structures for compounds in the classes studied;
  3. propose and draw mechanistic pathways which illustrate how the products are obtained from the reactants;
  4. evaluate kinetic data as a tool in elucidating the mechanism for a reaction;
  5. name compounds of the classes studied;
  6. carry out syntheses in the laboratory, using techniques developed in Chemistry 12A to monitor the progress of the reaction and the purity of the product;
  7. identify an unknown organic compound in the laboratory by chemical methods and spectroscopic methods;
  8. utilize carbanion chemistry in proposing sophisticated syntheses;
  9. apply knowledge of organic reactions to biological processes;
  10. develop qualitative and quantitative problem solving techniques;
  11. effectively communicate observations and subsequent conclusions by means of written laboratory notebooks and report.
Course Content:

 

Course Content (Lecture):

  1. Dienes:
    1. Structure and properties
    2. Resonance theory and stability of dienes
    3. Electrophilic addition to conjugated dienes; 1,4 addition
    4. Kinetic vs. thermodynamic products (1,2  vs. 1,4 addition)
    5. Polymerization of dienes
    6. Isoprene and the isoprene rule
    7. The Diels-Alder reaction
  2. Aromaticity:
    1. Benzene; structure and resonance
    2. Aromatic character; the Huckel 4n+2 rule
    3. Reactions of benzene
    4. Electrophilic aromatic substitution mechanism, including reactivity and orientation
    5. Synthesis of substituted benzenes
    6. fElectrophilic substitution in naphthalene
  3. Arenes and Their Derivatives:
    1. Structure and properties
    2. Nomenclature
    3. Reactions of alkylbenzenes
    4. Preparation and reactions of alkenylbenzenes
  4. Phenols:
    1. Structure and properties
    2. Nomenclature
    3. Structure and relationship to acid strength
    4. Laboratory preparations of phenols
    5. Reactions of phenols
  5. Aryl Halides:
    1. Structure and properties
    2. Nomenclature
    3. Laboratory preparations of aryl halides
    4. Reactions of aryl halides
    5. Detailed analysis of nucleophilic aromatic substitution reactions, including both bimolecular displacement and elimination-addition mechanisms
  6. Aldehydes and Ketones:
    1. Structure and properties
    2. Nomenclature
    3. Laboratory preparations of aldehydes and ketones
    4. Reactions of aldehydes and ketones
    5. Detailed analysis of nucleophilic addition
    6. Multi-step syntheses of aldehydes, ketones and related compounds
  7. Carboxylic Acids:
    1. Structure and properties
    2. Nomenclature
    3. Acidity and relationship to structure
    4. Laboratory preparations of carboxylic acids
    5. Reactions of carboxylic acids
  8. Functional Derivatives of Carboxylic Acids:
    1. Nucleophilic acyl substitution reactions
    2. Mechanism of nucleophilic acyl substitutions and comparison to alkyl nucleophilic substitutions
    3. Structure, nomenclature, preparation and reactions of acid chlorides
    4. Structure, nomenclature, preparation and reactions of acid anhydrides
    5. Structure, nomenclature, preparation and reactions of amides
    6. Structure, nomenclature, preparation and reactions of esters
  9. Amines:
    1. Structure and properties
    2. Nomenclature
    3. Structure and relationship to base strength
    4. Sterochemistry of nitrogen
    5. Laboratory preparations of amines
    6. Reactions of amines
  10. Heterocyclic Compounds:
    1. Structure and properties of pyrrole, furan and thiophene and pyridine
    2. Electrophilic substitution in heterocyclic compounds
    3. Nucleophilic substitution in pyridine
  11. Carbanion Chemistry:
    1. Aldol condensations
    2. Claisen condensations
    3. Wittig reactions
    4. Malonic ester synthesis of carboxylic acids
    5. Acetoacetic ester synthesis of ketones
    6. Stork reaction of enamines
    7. Use of the above reactions in multi-step syntheses
  12. Alpha-beta unsaturated Compounds:
    1. Structure and properties
    2. Laboratory preparations
    3. Electrophilic and nucleophilic addition reactions
    4. Michael additions
  13. Biomolecules:
    1. Carbohydrates
    2. Classifications, Fischer Projections and configurations
    3. Cyclic structures of monosaccharides, hemiacetal formation
    4. Monosaccharide anomers and mutarotation
    5. Reactions of monosaccharides (Kiliani-Fishcher synthesis and The Ruff Degradation)
    6. Disaccharides and polysaccharides
  14. Amino acids and Proteins
    1. Structure and properties of amino acids including isoelectric points
    2. Synthesis of alpha amino acids
    3. Peptide bonds
    4. Peptide sequencing (Edman Degradation and C-Terminal Residue Determination Technique)
    5. Peptide synthesis
    6. Proteins, structure and denaturation
    7. Enzymes
  15. Lipids
    1. Structure and properties of waxes, fats and oils
    2. Phospholipids, structure and use in cell membranes
    3. Structure and biosyntheses of terpenes and steroids

Course Content (Laboratory):

  1. Techniques:
    1. Boiling point and melting point determinations
    2. Extraction
    3. Crystallization
    4. Refractometry
    5. Simple and vacuum distillations
    6. Gas chromatography
    7. Multi-step syntheses
  2. Qualitative Analysis:
    1. Wet chemistry analysis of unknowns including formation and purification of derivatives for elucidating molecular structure.
    2. Interpretation of IR and NMR spectra for elucidating molecular structures.
    3. Library  and Internet Research
Methods of Instruction:
  1. Demonstrations and computer simulations
  2. Hands-on laboratory work with direct access to all instrumentation
  3. Lecture/Discussion
  4. Distance Education
  5. Models, computerized molecular modeling, videos, and transparencies
Assignments and Methods of Evaluating Student Progress:
  1. Read the chapter on carboxylic acids in your text and 1) complete all the designated end of the chapter problems 2) design a separation scheme to separate benzoic acid from a mixture with naphthalene using the acidity and solubility of benzoic acid and the benzoate ion.
  2. Propose a synthesis of 4-nitro-2,6-dibromoanisole from anisole
  3. Draw all resonance structures for the sigma complex formed during the para attack of an electrophile on aniline.
  1. Quizzes
  2. Exams/Tests
  3. Home Work
  4. Oral Presentation
  5. A minimum of 5 formal written laboratory reports based on departmentally approved experiments and graded on criteria that may include the following 1) Description of experimental procedures 2) Completeness of data collected 3) Quality of data collected 4) Computational precision and accuracy 5) Accuracy and precision of experimental laboratory results 6) Proper use of symbolic notation 7) Quality of analysis of scientific principles explored 8) Quality of narrative explanations and reasoning 9) Representation of data in tables or diagrams
  6. Written laboratory notebook graded on criteria that may include the following 1) Description of experimental procedures 2) Completeness of data collected 3) Quality of data collected 4) Computational precision and accuracy 5) Accuracy and precision of experimental laboratory results 6) Proper use of symbolic notation 7) Quality of analysis of scientific principles explored 8) Quality of narrative explanations and reasoning 9) Representation of data in tables or diagrams
  7. Final Examination
  8. Written assignments that encourage critical thinking and writing skills
Upon the completion of this course, the student should be able to:
  1. (Critical Thinking) Analyze experimental data and explain chemical processes at the molecular level.
  2. (Communication) Communicate chemical concepts, understand definitions, and interpret experimental results.
  3. (Development of the Whole Person) Recognize and appreciate the impact of the scientific principles of chemistry in day-to-day life
Textbooks (Typical):
  1. Carey and Giuliano (2014). Organic Chemistry (9th). McGraw-Hill.
  2. Pavia, Lampman, Kriz and Engel (2011). Introduction to Organic Laboratory Techniques, a Microscale Approach (5th). Thomson Brooks/Cole.
  • Molecular model kit
  • Scientific calculator
  • Safety goggles approved for Chemistry laboratory
  • Laboratory coat/apron
Abbreviated Class Schedule Description:
Introduction to the chemistry of dienes, aromatics, amines, carbanions, carboxylic acids, carboxylic acid derivatives, aldehydes, ketones and biochemical topics focusing on structure, synthesis, and mechanisms of reaction. Laboratory work in basic techniques, synthetic methods, qualitative, spectroscopic, and chromatographic analysis techniques. Chemistry 12B is the second semester in a year course in Organic Chemistry designed for students majoring in Chemistry related disciplines.
Prerequisite: CHEM 12A.
Discipline:
Chemistry*