Course Outline for Chemistry 12A
Organic Chemistry I

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

CHEM 12A - Organic Chemistry I

5.00 Units

Hydrocarbons, alkyl halides, alcohols, ethers, and an introduction to aromatic hydrocarbons. Structure, bonding, stereochemistry, conformational analysis, nomenclature, and physical properties in relation to these particular groups of compounds. Emphasis on reactivity and reaction mechanisms. Laboratory work includes microscale, macroscale, spectroscopic, and chromatographic techniques. Chemistry 12A is the first semester in a year long course in organic chemistry designed for students majoring in chemistry and related disciplines.
Prerequisite: CHEM 1B.
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. name compounds of the common organic functional groups using the IUPAC system of nomenclature;
  2. use a mechanistic approach to make reasonable predictions of major products formed in reactions involving hydrocarbons, alkyl halides, alcohols and ethers;
  3. explain physical and chemical properties of groups studied based on structural analysis;
  4. use spectroscopic data from infrared spectroscopy, 1H nuclear magnetic spectroscopy to elucidate structures for organic compounds;
  5. identify structural isomers, stereoisomers and conformers and determine relationships between pairs of structures;
  6. predict and draw the possible conformations of acyclic and cyclic organic compounds and analyze these conformation for relative stability;
  7. identify stereocenters and chiral molecules and determine stereochemical relationships between pairs of compounds;
  8. use resonance theory and/or molecular theory to interpret reactivity of organic compounds;
  9. suggest plausible single step and multi-step syntheses of hydrocarbons, alcohols, alkyl halides and ethers;
  10. analyze and explain nucleophilic substitutions reactions via SN1 and SN2 mechanisms, including the influence of changes in structure of substrate and solvent;
  11. analyze and explain elimination reactions via E1 and E2 mechanisms, including the influence of changes in structure of substrate and solvent;
  12. develop qualitative and quantitative problem solving skills;
  13. perform basic laboratory techniques in organic laboratory: crystallization, simple and fractional distillation, melting and boiling point determinations, extractions, chromatography, and spectroscopy analysis;
  14. explain the theory behind the techniques of crystallization, melting point determination, extraction, distillation, boiling point determination and chromatographic separations;
  15. synthesize, separate and analyze organic compounds using microscale and semi-microscale methods;
  16. effectively communicate observations and subsequent conclusions by means of keeping a bound laboratory notebook and written laboratory reports;
  17. utilize library and internet resources for information and in support of laboratory reports;
  18. follow safe practices in handling and disposing of organic chemicals.
Course Content:

Course Content (Lecture):

  1. Review of General Chemistry Concepts:
    1. Atomic structure and electron configurations
    2. Bonding, hybrid orbitals and molecular shapes
    3. Molecular structure and relationship to physical properties (boiling point, solubility, etc).
    4. Acid/base theories
    5. Determination of empirical and molecular formulas from quantitative analysis
  2. Overview of Organic Chemistry:
    1. Structure of major functional groups including hydrocarbons, alkyl halides, alcohols, ethers, carbonyl compounds, amines and amides
    2. Nomenclature of above functional groups
  3. Alkanes:
    1. Structure and physical properties
    2. Sources of alkanes and industrial preparations
    3. Laboratory preparations of alkanes
    4. Reactions of alkanes including free radical halogenation
    5. Detailed analysis of use of kinetics and mechanisms
    6. Conformational analysis of open chain alkanes
    7. Structure of cycloalkanes, including stability and conformational analysis
    8. Stereochemistry of cycloalkanes
    9. Preparation and reactions of cycloalkanes
  4. Stereochemistry:
    1. Polarimetry and optical activity
    2. Chiral carbons and chiral substances
    3. Enantiomers, diastereomers and racemic modifications
    4. Specification of configuration, R/S
    5. Synthesis and optical purity
    6. Stereospecific reactions
    7. Stereoselectivity vs. stereospecificity
  5. Alkyl Halides:
    1. Structure and physical properties
    2. Laboratory preparations of alkyl halides
    3. Reactions of alkyl halides
    4. Detailed analysis of nucleophilic substitution reactions (SN1 and SN2 mechanisms)
    5. Solvent effects and secondary bonding
    6. Carbocations and rearrangements
  6. Alcohols:
    1. Structure and physical properties
    2. Industrial sources
    3. Laboratory preparations of alcohols
    4. Reactions of alcohols
    5. Multi step synthesis of alcohol
  7. Ethers:
    1. Structure and physical properties
    2. Laboratory preparation of ethers
    3. Reactions of ethers
  8. Spectroscopy:
    1. Introduction to Mass Spectroscopy and use in determining molar mass and molecular formulas
    2. Infrared Spectroscopy and use in elucidating basic molecular structures
    3. 1H Nuclear Magnetic Resonance and use in elucidating molecular structures
  9. Alkenes:
    1. Structure and properties
    2. Geometric Isomerism including specification of E/Z configurations
    3. Laboratory preparations of alkenes
    4. Detailed analysis of elimination reactions (E1 and E2 mechanisms)
    5. Stereochemistry of E2 reactions, syn  and anti elimination
    6. Competition between elimination and substitution
    7. Reactions of alkenes
    8. Detailed analysis of addition reactions (electrophilic and free radical)
    9. Stereochemistry of addition reactions, syn  and anti addition
    10. Free radical addition and substitution in alkenes including allylic rearrangements
  10. Alkynes:
    1. Structure and properties
    2. Laboratory preparation of alkynes
    3. Reactions of alkynes (including introduction of tautomerism via hydration)
    4. Acidity of alkynes

Course Content (Laboratory):

  1. Techniques:
    1. Boiling Point and Melting Point Determination
    2. Extraction
    3. Simple and Fractional Distillation
    4. Polarimetry
    5. Crystallization 
    6. Thin layer and column chromatography
    7. Refractometry
    8. Vacuum Sublimation
    9. Infrared Spectroscopy
    10. Synthesis of simple compounds
  2. Safety:
    1. Correct handling of organic compounds
    2. Use of literature (Reference books such as Merck Index, etc and MSDS sheets) and internet resources to determine possible hazards and safe handling procedures
Methods of Instruction:
  1. Demonstrations and computer simulations
  2. Hands-on laboratory work with direct access to all instrumentation
  3. Lecture/Discussion
  4. Problem Solving
  5. Distance Education
  6. Models, computerized molecular modeling, videos, and transparencies
Assignments and Methods of Evaluating Student Progress:
  1. Read the chapter on alkanes in your text and 1) complete all the designated end of the chapter problems 2) using models, complete the assignment on conformations.
  2. Synthesize acetylsalicylic acid, otherwise known as aspirin, and 1) purify your product by crystallization using water as solvent 2) calculate the percent yield for your reaction 3) obtain the melting point of your product and compare it to the literature value. Cite your literature reference.
  1. Quizzes
  2. Exams/Tests
  3. Home Work
  4. 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
  5. Written laboratory notebooks 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. Final Examination
  7. 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 (2012). Introduction to Organic Laboratory Techniques, a Microscale Approach (5th). Thomson Brooks/Cole.
  • Molecular model kit
  • Scientific calculator
  • Safety goggles approved for chemistry laboratory
  • Laboratory notebook with sewn-in pages
Abbreviated Class Schedule Description:
Hydrocarbons, alkyl halides, alcohols, ethers, and an introduction to aromatic hydrocarbons. Structure, bonding, stereochemistry, conformational analysis, nomenclature, and physical properties in relation to these particular groups of compounds. Emphasis on reactivity and reaction mechanisms. Laboratory work includes microscale, macroscale, spectroscopic, and chromatographic techniques. Chemistry 12A is the first semester in a year long course in organic chemistry designed for students majoring in chemistry and related disciplines.
Prerequisite: CHEM 1B.
Discipline:
Chemistry*