CHEM 252 - Organic Chemistry II
5 Credit: (3 lecture, 3 lab, 0 clinical) 6 Contact Hours: [CHEM 251 ]
This course focuses on ethers, carbonyl compounds, aldehydes and ketones, carboxylate derivatives, conjugation, aromaticity, amino acids, proteins, carbohydrates, and nucleic acids. Concurrent laboratory will focus on the multistep synthesis of various organic compounds and their spectral analysis.
OFFERED: as needed
Course Goals/ Objectives/ Competencies:
Goal 1: Describe “aromaticity” and reactions of benzene and substituted benzenes.
- Describe the stable nature of aromatic compounds
- Apply the criteria (two) for aromaticity
- Examine various heterocyclic compounds for aromaticity
- Recite the consequences of aromaticity and depict the molecular orbital for aromaticity and antiaromaticity
- Name various monosubstituted benzenes
- Describe, using a mechanistic approach (Electrophilic Aromatic Substitution), the following reactions of benzene:
- iv. Friedel-Crafts Acylation
- v. Friedel-Crafts Alkylation
- vi. Alkylation by acylation-reduction
- Demonstrate coupling reactions
- Name and write formulas for di- and polysubstituted benzenes
- Explain how substituents can increase or decrease benzene ring reactivity
- Describe the effect that substituents have on the pKa of aromatic compounds
- Describe the synthesis of mons, di, and trisubstituted benzenes
- Examine the addition-elimination mechanisms for nucleophilic aromatic substitution
Goal 2: Demonstrate a thorough understanding of carbonyl compounds and their various reactions.
- Describe the structural and physical properties of carbonyl compounds, including carboxylic acids (and their derivatives), aldehydes, and ketones
- Recite the nomenclature of carbonyl compounds
- Explain the mechanism for Nucleophilic Acyl Substitution reactions
- Predict the products of carbonyl compounds and acyl halides, acid anhydrides, esters, amides imides, and nitriles.
- Describe characteristics of soaps, detergents, and Micelles
- Describe reactions of aldehydes and ketones
- Describe reactions of carbonyl compounds with Grignard Reagents, acetylide ions, and hydride ions.
- Describe reactions of aldehydes and ketones with HCN, amines, water, and alchols.
- Explain the function of protecting groups in organic reactions
- Predict the product(s) of the Wittig reaction.
- Identify the products of Nucleophilic Addition reactions of aldehydes, ketones, and carboxylic acid derivatives.
- Discuss the acidity of an alpha hydrogen
- Explain and differentiate between Keto-Enol Tautomers, Enolization, and their reactivity
- Describe reactions at the α-carbon of aldehydes, ketones, and carboxylic acids
- Describe mixed aldol addition, Claisen condensation, Malonic ester synthesis, and acetoacetic ester synthesis.
Goal 3: Investigate oxidation-reduction reactions of organic compounds and reactions of amines.
- Predict the products of the oxidation of alcohols, aldehydes, ketones, diols, amines, alkenes, and alknyes.
- Recite the nomenclature of amine compounds
- Generalize how amines act as bases and nucleophiles
- Describe properties of aromatic amines
Goal 4: Recognize bioorganic compounds and describe the properties of carbohydrates, amino acids, peptides, and proteins.
- Classify carbohydrates and recognize the D and L forms
- Examine various reactions of monosaccharides
- Distinguish between aldoses and ketoses
- Identify lengthening chain reactions (Kiliani-Fisher synthesis) and shortening chain reactions (Wohl Degradation reaction)
- Describe the formation of cyclic hemiacetals
- Recognize glycosides and their formation
- Distinguish between reducing and nonreducing sugars
- Explain the anomeric effect
- Summarize the classification and nomenclature of amino acids
- Recognize the acid-base properties of amino acids
- Differentiate between peptide and disulfide bonds
- Recognize secondary, tertiary, and quaternary structures of proteins
Goal 5: Demonstrate techniques involved in the laboratory separation, analysis, synthesis, and purification of organic compounds.
- Describe the essential features of mass spectroscopy and interpret a mass spectrum
- Describe the essentials features of infrared spectroscopy and interpret an IR spectrum
- Describe the essential features of visible and UV spectroscopy
- Review the Beer-Lambert Law
- Describe the essential features of H NMR spectroscopy and interpret an H NMR spectrum
- Describe C-13 NMR spectroscopy
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