Organic Chemistry I and Organic Chemistry II

Instructors: Dr. Jan Milecki (Lecture) and Jacob Garjewski (Laboratory)

Consultants: NCSU faculty members Dr. Kay Sandberg and Dr. Maria Gallardo-Williams will provide web-based materials based on the design at NCSU. This course is based on CH221 and 223 (lectures for I and II, respectively) and CH222 and CH224 (laboratories for I and II, respectively). The lectures and laboratories are 3 and 1 credits, respectively.

The corresponding ISU courses are Chem331, 332 and the laboratories are Chem331L and 332L.

Organic Chemistry I Lecture

1	Organic structures and Alkanes
2	Alkane nomenclature
3	More alkane nomenclature and physical properties of alkanes
4	Combustion of alkanes, bicycloalkanes, conformations of alkanes
5	Cyclohexane chemistry
6	Acid base chemistry & Alkyl halide and alcohol introduction
7	SN1 mechanism & carbocation stability
8	Halogenation of alkanes
9	Spectroscopy: NMR
Exam 1	Lectures 1 – 8
10	Alkenes: nomenclature, physical properties, E1 rxn
11	Alkene Preparations: Dehydration & dehydrohalogenation
12	NMR with pi-systems and IR
13	Alkene addition rxns - electrophilic addition & free-radical addition
14	More alkene addition reactions
15	More alkene reactions: Polymerization & Ozonolysis; Chirality
16	Chirality: R/S configuration determination
Exam 2	Lectures 9 – 15
17	Chirality: reactions
18	The SN2 mechanism
19	Predicting which of the 4 mechanisms leading to the MOP
20	Ethers and sufides
21	Epoxide chemistry
22	Alcohol synthesis & carbonyl reduction
23	Diol synthesis & alcohol oxidation
Exam 3	Lectures 16 – 22
24	Thiol chemistry & introduction to alkynes
25	Alkynes –preparations & reactions
26	Alkyne reactions

Organic Chemistry I Laboratory

Day	Experiment
	Safety Briefing Introduction to the Lab
	Experiment 1: Thin Layer Chromatography
	Experiment 2: Infrared Spectroscopy
	Experiment 3: Extraction
	Experiment 4: Dehydration of an Alcohol/ Gas Chromatography
	Experiment 5: Nucleophilic Substitution: The SN2 Reaction Final Written Quiz Laboratory Cleanup and Checkout

Learning Outcomes

Upon successful completion of this course, the student will be able to: 

1. Become aware of the safety procedures and regulations that must be observed when performing organic chemistry experiments in a laboratory.  

2. Perform simple separations using Thin Layer Chromatography. 

3. Determine melting points and boiling points and use them to characterize organic compounds. 

4. Perform Infrared Spectroscopy and use the results obtained to identify organic compounds. 

5. Accomplish the separation of predetermined chemical mixtures by using liquid-liquid extraction and microextraction.

6. Complete small-scale synthesis of simple organic materials and characterize the products obtained using a variety of techniques.  

7. Use Gas Chromatography as a tool for separation and characterization of organic materials. 

8. Combine the use of different synthetic and separation methods in order to execute multi-step synthesis.

Organic Chemistry II Lecture

1	Conjugation: allylic systems
2	Conjugation: dienes, Diels-Alder reaction
3	Aromaticity: properties, nomenclature, benzylic bromination
4	Aromaticity: attributes that make a system aromatic
5	Alkenylbenzene reactions & Birch reduction
6	Electrophilic aromatic substitution
7	EAS: substituent effects
8	Organometallic chemistry
Exam 1	Lectures 1 – 7
9	Carbonyl reductions to alcohols & alcohol oxidations to carbonyls
10	More aldehyde & ketone chemistry, hydration, cyanohydrin
11	Carbonyl reactions: hemiacetal & acetal
12	Carbonyl reactions: imines, enamines, Wittig, enol
13	Enol and enolate ion chemistry
14	Alpha-beta unsaturated carbonyl chemistry, carboxylic acid intro
15	Carboxylic acid reactions
16	Carboxylic acid derivatives
Exam 2	Lectures 8 – 15
17	Carboxylic acid derivatives – esters & amides
18	Nitrile chemistry & ester enolates
19	Ester enolates in synthesis
20	Amines – nomenclature & properties
21	Amines – preparations & reactions
22	Arylamine reactions & aryl halide reactions
23	NAS & phenol chemistry
Exam 3	Lectures 16 – 22
24	Phenol reactions & sugars
25	Select biochem topics
26	Select biochem topics

Organic Chemistry II Laboratory

Experiment

Introduction to the Lab

Exp 1: Literature Search Assignment

Exp 2: NMR Spectroscopy

Exp 3: Reduction of a Ketone

Exp 4: Oxidation of Acetophenone

LABORATORY QUIZ 1

Exp 5: Nitration of Methyl Benzoate

Exp 6: Aldol Condensation

Exp 7: Preparation of 1,4-diphenyl-1,3-Butadiene

Exp 8: Amide Preparation

Exp 9: Arenediazonium Salts

Exp 10: Hydrolysis of Glycerol Tristearate

Laboratory Quiz 2

Laboratory Cleanup and Checkout