CHEM 2310

Organic Chemistry I

Salt Lake Community College

Ron Valcarce

Office SI 215   Phone: 957-4830

Office Hours
9:00 -9:50 a.m.,  M-F (or by appointment)

IMPORTANT DATES - Fall Semester 2017

August 23rd (W) First Day of Class

August 31st (H) Last Day to Add Classes

September 4th (M) Labor Day Holiday, No Class

September 13th (W) Last Day to Drop Class with100% Refund

October 19th & 20th (H & F) Fall Break, No Class

October 25st (W) Last Day to Withdraw*
*Please see me before withdrawing from class

November 23rd & 24th (H & F) Thanksgiving Holiday, No Class

December 7th (H), Last Day of Class

December 8th (F), Make-Up Tests day for 2310

Fall Semester 2017

CHEM 2310-400, (CRN-40343)
MTWR, 10:00-10:50 A.M., SI 291

CHEM 2310-401, (CRN-40344)
MW, 12:30-2:10 P.M., SI 291

Problem Solving - Highly recommended, but not required for this class

CHEM 2318-400 (CRN-41034)

F, 10:00-10:50 A.M., SI 265


F, 12:00-10250 P.M., SI 285

Text Textbook

Organic Chemistry, Francis  A. Carey 9th edition Chapters 1 – 10 & 13

Student Solutions Manual for Organic Chemistry,Francis A. Carey, 9th edition*

*Make sure your solutions manual edition matches the text book edition.

The study guide is required for this class


We will have ten (9) chapter exams, each worth 90 points.  

Make-up exams will be given for appropriate medical or family emergencies.  All make-up exams will be scheduled on 12/08.  

We will also have a spectroscopy project worth 90 points.


midterm exams                 810 points      
spectroscopy Project         90 points
Total                                  900 Points Possible

                  100% - 94%    A       

                    93% - 90%    A-

                    89% - 87%    B+

                    86% - 83%    B        

                    82% - 80%    B-

                    79% - 77%    C+

                     76% - 73%    C


You cannot successfully learn organic chemistry without spending a considerable amount of time working end of chapter problems.   

Homework will count for 20 point of each exam and will consist of working ALL the end-of-chapter problems in the text book and the ALL the Self-Test problems in the solutions manual.  Homework is due with each exam.

Extra Credit

Students may earn up to 3% extra credit by participating with the ACS-Student Affiliates Chemical Information Series.  More information will be given in class

Instructor reserves the right to change or modify any content in this syllabus or the course schedule.

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Organic Chemistry 2310 Learning Objectives by Chapter Topics:

Chapter 2 - Alkanes and Cycloalkanes: Introduction to Hydrocarbons

Classes of Hydrocarbons
Electron Waves and Chemical Bonds; the Valence Bond Model
Introduction to Alkanes: Methane, Ethane, and Propane
Hybridization and Bonding in Methane & Ethane
Isomeric Alkanes
IUPAC Nomenclature of Unbranched Alkanes - Applying the IUPAC Rules
Nomenclature of Alkyl Groups
IUPAC Names of Highly Branched Alkanes & Cycloalkanes
Sources of Alkanes and Cycloalkanes
Physical Properties of Alkanes and Cycloalkanes
Chemical Properties: Combustion of Alkanes - Thermochemistry
Oxidation-Reduction in Organic Chemistry
sp2 Hybridization and Bonding in Ethylene
sp Hybridization and Bonding in Acetylene

Chapter 3 - Conformations of Alkanes and Cycloalkanes & an Introduction to Stereochemistry

Conformational Analysis of Ethane & Butane
Conformations of Higher Alkanes
The Shapes of Cycloalkanes: Cyclopropane, Cyclobutane, Cyclopentane & Cyclohexane
Axial and Equatorial Bonds in Cyclohexane
Conformational Inversion in Cyclohexane
Conformational Analysis of Monosubstituted Cyclohexanes
Disubstituted Cyclohexanes: cis-trans Stereoisomers
Conformational Analysis of Disubstituted Cyclohexanes
Conformations of Medium and Large Rings
Polycyclic Ring Systems; spirocyclic and bicyclic rings
Heterocyclic Compounds

Chapter 4 - Alcohols and Alkyl Halides: Introduction to Reaction & Reaction Mechanisms

Organic Functional Groups
IUPAC Nomenclature of Alkyl Halides & Alcohols
Classes of Alcohols & Alkyl Halides
Bonding in Alcohols & Alkyl Halides
Physical Properties of Alcohols and Alkyl Halides: Intermolecular Forces
Preparation of Alkyl Halides from Alcohols and Hydrogen Halides: the Sn substitution reaction
Mechanism of the Sn2 substitution reaction & Hammond’s Postulate
Mechanism of the Sn1 substitution reaction
Potential Energy Diagrams for Multistep Reactions:
Structure, Bonding, and Stability of Carbocations
Effect of Alcohol Structure on Reaction Rate
Activation Energy
Inorganic Methods for Converting Alcohols to Alkyl Halides
Free Radical Halogenation of Alkanes
Mechanism of Free-Radical halogenation of Methane
Structure and Stability of Free Radicals
Halogenation of Higher Alkanes

Chapter 5 - Alkenes: Structure and Preparation by Elimination Reactions 

Alkene IUPAC Nomenclature
Structure and Bonding in Alkenes (sp2 hybridized systems)
Isomerism in Alkenes (Cis/Trans & E/Z stereoisomers)
Naming Stereoisomeric Alkenes by the E-Z Notational System
Physical Properties of Alkenes
Relative Stabilities of Alkenes (Zaitsev’s order)
Preparation of Alkenes: b-Elimination Reactions
Dehydration of Alcohols
Regioselectivity in Alcohol Dehydration: The Zaitsev Rule
Stereoselectivity in Alcohol Dehydration
The E1 and E2 Mechanisms of Alcohol Dehydration
Rearrangements in Alcohol Dehydration Reactions – Hydride and alkyl Shifts
Dehydrohalogenation of Alkyl Halides
The E2 Mechanism of Dehydrohalogenation of Alkyl Halides
Anti Elimination in E2 Reactions: Stereoelectronic Effects
Isotope Effects and the E2 Mechanism
The E1 Mechanism of Dehydrohalogenation of Alkyl Halides with Weak Bases

Chapter 6 - Addition Reactions of Alkenes

Hydrogenation of Alkenes - Heats of Hydrogenation
Mechanism of Hydrogenation of Alkenes
Stereochemistry of Alkene Hydrogenation
Electrophilic Addition of Hydrogen Halides to Alkenes
Regioselectivity of Hydrogen Halide Addition: Markovnikov’s Rule
Mechanistic Basis for Markovnikov’s Rule
Carbocation Rearrangements in Hydrogen Halide Addition to Alkenes
Addition of Sulfuric Acid to Alkenes
Acid-Catalyzed Hydration of Alkenes
Mechanism of Acid-Catalyzed Hydration
Thermodynamics of Addition-Elimination Equilibria
Hydroboration-Oxidation of Alkenes
Stereochemistry of Hydroboration-Oxidation
Mechanism of Hydroboration-Oxidation
Addition of Halogens to Alkenes
Stereochemistry of Halogen Addition
Mechanism of Halogen Addition to Alkenes: Halonium Ions
Conversion of Alkenes to Vicinal Halohydrins
Free-Radical Addition of Hydrogen Bromide to Alkenes
Mechanism Free-Radical Addition of Hydrogen Bromide
Epoxidation of Alkenes
Ozonolysis of Alkenes
Ethylene and Propene: The Most Important Industrial Organic Chemicals

Chapter 7 - Stereochemistry & Chirality 

Molecular Chirality: Enantiomers
Sp3 Carbon Chirality Center
Chirality Centers & Points/Planes of Symmetry in Achiral Structures
Properties of Enantiomers & Optical Activity
The Cahn-Ingold-Prelog R-S Notational System
Fischer Projections
Reactions That Create a Chirality Center
Chiral Molecules with Two Chirality Centers – Enantiomers & Diastereomers
Achiral Molecules with Two Chirality Centers
Molecules with Multiple Chirality Centers
Chirality of Disubstituted Cyclohexanes
Reactions That Produce Diastereomers
Resolution of Enantiomers
Chirality Centers Other Than Carbon
Chiral Drugs

Chapter 8 - Nucleophilic Substitution

Functional Group Transformation by Nucleophilic Substitution
Relative Reactivity of Halide Leaving Groups
The SN2 Mechanism of Nucleophilic Substitution
Steric Effects in SN2 Reaction Rates
Nucleophiles and Nucleophilicity
The SN1 Mechanism of Nucleophilic Substitution
Carbocation Stability and SN1 Reaction Rates
Stereochemistry of SN1 Reactions
Carbocation Rearrangements in SN1 Reactions
Effect of Solvent on the Rate of Nucleophilic Substitution
Mechanism Carbocation Rearrangement in the SN1 Reaction
Substitution and Elimination as Competing Reactions
Nucleophilic Substitution and Elimination of Alkyl Sulfonates

Chapter 9 - Alkynes 

Sources of Alkynes
Physical Properties of Alkynes
Structure and Bonding in Alkynes: sp Hybridization
Acidity of Acetylene and Terminal Alkynes
Preparation of Alkynes by Alkyation of Acetylene and Terminal Alkynes
Preparation of Alkynes by Elimination Reactions
Addition Reactions of Alkynes
Hydrogenation of Alkynes
Metal-Ammonia Reduction of Alkynes
Addition of Hydrogen Halides to Alkynes
Hydration of Alkynes
Addition of Halogens to AlkynesOzonolysis of Alkynes

Chapter 10 - Conjugation in Alkadienes and Allylic Systems

The Allyl Group
Allylic Carbocations
SN1 Reactions of Allylic Halides
SN2 Reactions of Allylic Halides
Allylic Free Radicals
Allylic Halogenation
Allylic Anions
Classes of Dienes
Relative Stabilities of Dienes
Bonding in Conjugated Dienes & Allenes
Preparation of Dienes & Diene Polymers
Addition of Hydrogen Halides to Conjugated Dienes
Halogen Addition to Dienes
The Diels-Alder Reaction

Intropduction to Spectroscopy

Principles of Molecular Spectroscopy: Electromagnetic Radiation & Quantized Energy States
Introduction to Infrared Spectroscopy
Infrared Spectra - Characteristic Absorption Frequencies
Interpreting Infrared Spectra
Introduction to H-NMR Spectroscopy
Nuclear Shielding and H-NMR Chemical Shifts
Effects of Molecular Structure on H-NMR Chemical Shifts
Ring Currents—Aromatic and Antiaromatic
Interpreting H-NMR Spectra
Spin-Spin Splitting in H-NMR Spectroscopy: The Ethyl Group, Isopropyl Group & tert-Butyl Group
13-C NMR Spectroscopy
13-C Chemical Shifts and Peak Intensities
H-NMR Coupling
Mass Spectrometry
Interpreting the Mass Spectrum
Molecular Formula as a Clue to Structure



Subpages (1): Practice Exams - 2310