CHEM 2211 Syllabus

Subject Code

CHEM

Course Number

2211

Course Title

Organic Chemistry I

Prerequisites

CHEM 1211 with a grade of C or higher, CHEM 1211L with a grade of C or higher

Corequisites

CHEM 2211L

Terms Offered

Credit Hours

Course Description

This course is the first of a two-semester sequence of organic chemistry. Topics include structure, bonding, stereochemistry, and reactions of organic molecules comprised of alkanes, cycloalkanes, alkenes, alkynes, and organohalides.

Course Outcomes

Structure and Bonding

  • Examine atomic structure, the nucleus, orbitals, and electron configuration.
  • Express valence bond theory.
  • Differentiate hybrid orbitals.
  • Express molecular orbital theory.
  • Examine chemical structures.
  • Evaluate polar covalent bonds and their electronegativity, dipole moments, formal charges, and resonance.
  • Differentiate acids and bases.

Organic Structure: Alkanes, Cycloalkanes, and Their StereoChemistry

  • Compare functional groups.
  • Classify alkanes, isomers, and groups.
  • Examine nomenclature of alkanes and cycloalkanes.
  • Compare properties of alkanes and cycloalkanes.
  • Evaluate Cis-Trans isomerism in cycloalkanes.
  • Examine stability and conformations of cycloalkanes.
  • Differentiate axial and equatorial bonds in cycloalkanes.

Overview of Organic Reactions

  • Compare types of reactions.
  • Differentiate mechanisms.
  • Predict reactions using equilibria, rates, energy changes, bond dissociation energies, energy diagrams, transition states, and intermediates.

Alkenes, Alkanes, and Conjugated Compounds: Their Structure, Reactivity and Synthesis

  • Evaluate degrees of unsaturation and name alkenes including Cis-Trans and E-Z designations. Name alkynes.
  • Examine stability of alkenes.
  • Evaluate electrophilic addition reactions of alkenes including orientation, Markovnikov's rule, carbocation structure and stability, Hammond postulate, and rearrangement.
  • Examine preparations of alkenes and alkynes by elimination.
  • Evaluate reactions of alkenes including addition of halogens and hydrogen halides, oxymercuration, hydroboration-oxidation, carbine addition, hydrogenation, epoxidation, hydroxylation, cleavage to carbonyl compounds, and radical additions.
  • Evaluate reactions of alkynes including addition of halides, hydrogen halides, and water; reductions; oxidative cleavage; alkyne acidity; and alkylation of acetylide ions.
  • Design organic synthesis.
  • Examine stability of conjugated dienes using Molecular Orbital Theory.
  • Evaluate electrophilic additions to conjugated dienes to differentiate between kinetic and thermodynamic control.
  • Examine the Diels-Alder reaction and its characteristics.
  • Examine natural and synthetic diene polymers.

Stereochemistry

  • Compare enantiomers at the tetrahedral carbon and examine chirality.
  • Evaluate optical activity including Pasteur's discovery of enantiomers and the sequence rules for specifying configuration.
  • Examine diastereomers, meso compounds, racemic mixtures, and the resolution of enantiomers.
  • Relate types of isomerism.
  • Examine reaction stereochemistry of addition of water to achiral and chiral alkenes.
  • Compare chirality at nitrogen, phosphorous, and sulfur.
  • Distinguish prochirality and analyze chirality in nature and chiral environments.

Organohalides and Their Reactions

  • Examine nomenclature of alkyl halides and examine their structures.
  • Evaluate preparation of alkyl halides from alkanes (radical Halogenation), alkenes (allylic bromination), and alcohols.
  • Examine the stability of allylic radicals.
  • Examine reactions of alkyl halides including Grignard reagents, organometallic coupling reactions, and oxidation/reduction concepts of organic chemistry.
  • Examine the discovery of nucleophilic substitution reactions.
  • Differentiate Sn1 and Sn2 reactions and their characteristics. Examine biological substitution reactions.
  • Examine elimination reactions of alkyl halides using Zaitsev's rule.
  • Evaluate the deuterium isotope effect and cyclohexane conformation on the E2 reaction.
  • Examine the E1 and E1cB reactions.
  • Examine biological elimination reactions.

Spectroscopy

  • Interpret mass spectrometry of small molecules, common functional groups, and biological molecules.
  • Compare and contrast infrared spectra.
  • Evaluate nuclear magnetic resonance spectroscopy. 
  • Interpret 13C NMR spectroscopy including: signal averaging, FT-NMR and DEPT.
  • Make sense of 1H NMR spectroscopy utilizing proton equivalence, chemical shifts, integration, and spin-spin coupling.
  • Interpret 1H NMR spectra.
  • Interpret ultraviolet spectra and the effect of conjugation.