CHO433 - Chemistry - Organic

Outline information
Semester
Schools offering this subject
Last revision date 2017-01-30 00:23:38.927
Last review date 2017-04-03 00:15:32.652

Subject Title
Chemistry - Organic

Subject Description
This is the continuation of CHO333 subject material. Stereochemistry, chemistry of benzene, aldehydes, ketones, carboxylic acids and their derivatives will be dealt with in detail. If time permits the chemistry of amines and amide linkage will also be covered in this subject.

Credit Status
The subject is worth one credit towards a diploma in the CHY, CHY-C, PMT and PMT-C programs.

PREREQUISITES: CHO333

Learning Outcomes
Upon successful completion of this subject the student will be able to:

A. LECTURE SECTION:
Upon successful completion of SESSION 1 of this course, the student will be able to:
? Describe the structure of benzene using resonance.
? Explain the bonding in benzene using the orbital hybridization model.
? Write a structural formula for an aromatic compound on the basis of its IUPAC name.
? Write a correct IUPAC name for an aromatic compound on the basis of a given structural formula.
? Write chemical equations describing the electrophilic aromatic substitution reactions of benzene: halogenation, nitration, sulfonation, Friedel-Crafts alkylation, and Friedel-Crafts acylation.
? Explain the mechanistic basis for the action of activating ortho, para-directing groups.
? Explain the mechanistic basis for the action of deactivating meta-directing groups.
? Explain why the halogens are deactivating ortho, para-directing groups.
? Write chemical equations describing the synthesis of disubstituted aromatic compounds.
? Write chemical equations for electrophilic addition and oxidation reactions of aromatic side chains.
? Predict whether a substance is aromatic based on its structure and H?ckel=s rule.
? Identify a chiral molecule by locating a chiral carbon atom.
? Explain what is meant by the term enantiomer, diastereomer.
? Draw perspective representations of chiral molecules.
? Draw Fischer projections of chiral molecules.
? Describe how a plane of symmetry relates to whether or not a molecule is chiral.
? Explain optical activity as a property of chiral molecules.
? Specify the absolute configuration of a molecule using the R-S notational system.
? Specify alkene stereochemistry using the E-Z notational system.
? Explain why addition reactions to achiral alkenes give racemic mixtures of products.
? Explain the meaning of the term meso isomer.
? Give the number of stereoisomers possible for a molecule having more than one chiral center.
? Describe how a racemic mixture may be resolved into individual enantiomers.

Upon successful completion of SESSION 2 of this course, the student will be able to:
? Provide an acceptable IUPAC name for an aldehyde or a ketone.
? Explain how the polarity of the carbonyl group affects physical properties of aldehydes and ketones.
? Describe how the polar nature of the carbonyl group affects nucleophilic additions to aldehydes and ketones.
? Write an equation for the hydration of an aldehyde or a ketone, for the formation of an acetal, for the formation of a cyanohydrin.
? Write chemical equations describing the reaction of an aldehyde or a ketone with derivatives of ammonia: primary amines and hydrazine derivative.
? Show how an organometallic compound can be used to form new carbon-carbon bonds.
? Describe by using chemical equations the reaction of a Grignard reagent with an aldehyde or a ketone.
? Plan the synthesis of a specific alcohol using a Grignard reagent.
? Explain the process of enolization and draw the enol form of a specific aldehyde or ketone.
? Write a chemical equation for the aldol condensation of an aldehyde.
? Write a chemical equation for the oxidation of an aldehyde.
? Provide an acceptable systematic IUPAC name for a carboxylic acid.
? Use chemical formulas to describe the hydrogen-bonding forces between carboxylic acid molecules.
? Write a chemical equation describing the acidity of a carboxylic acid.
? Write a mathematical equation representing the equilibrium constant for ionization of a carboxylic acid.
? Write a chemical equation describing the preparation of a carboxylic acid by carboxylation of a Grignard reagent, by hydrolysis of a nitrile.
? Write a chemical equation describing the formation of an acyl chloride from a carboxylic acid.
? Write a chemical equation describing the reduction of a carboxylic acid to give a primary alcohol.
? Give an acceptable systematic IUPAC name for a carboxylic acid derivative.
? Write the structure of a carboxylic acid derivative given its systematic name.
? Explain by using chemical equations the general mechanism for a nucleophilic acyl substitution reaction, and describe the role of the tetrahedral intermediate.
? Write a chemical equation for the preparation of an ester.
? Explain by using chemical equations the mechanism of the esterification process.
? Write chemical equations for the preparation of esters by using acyl chlorides or acetic anhydride.
? Write chemical equations for the acid-catalyzed and base-promoted hydrolysis of an ester.
? Explain by using chemical equations the reaction of an ester with a Grignard reagent.
? Describe by using chemical equations the preparation of an amide by the reaction of an amine with a carboxylic acid, an acyl chloride, acetic anhydride, or an ester.
? Write a chemical equation for the hydrolysis of an amide under both acidic and basic conditions.
B. Laboratory Section
? Learn how to balance redox reaction using organic and inorganic chemicals.
? Oxidize an alcohol to a ketone.
? Run an infrared spectrum of a ketone using a simple spectrophotometer and salt plates.
? Determine the equilibrium constant in an esterification reaction.
? Using Le Chatelier's principle drive an esterification reaction to completion.
? Learn how to operate a gas chromatograph and use it to separate isomers.
? To determine the product distribution in an alcohol dehydration experiment
? *To study the kinetics of the hydrolysis of benzoic acid esters. [*if time permits.]

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