Study-Unit Description

Study-Unit Description


TITLE Organic Chemistry 2

LEVEL 02 - Years 2, 3 in Modular Undergraduate Course



DESCRIPTION 1. Hydroxy Functional Group: Alcohols: Properties, Preparation, and Strategy of Synthesis
- Acid/base properties
- Synthesis of alcohols: Nucleophilic Substitution; Reduction of carbonyl groups; Grignard and other organometallics in the syntheses of alcohols
- Oxidation of alcohols
- Brief review of synthetic approaches to complex alcohols

2. Further Reactions of Alcohols and the Chemistry of Ethers
- Preparation and reactions of alkoxides
- Preparation of esters; use of inorganic esters in synthesis
- Synthesis of ethers: Williamson synthesis; dehydration of alcohols
- Reactions of ethers; oxacyclopropanes in synthesis
- Brief review of sulfur analogues of alcohols and ethers

3. Advanced Reactions of Alkenes
- Oxymercuration-Demercuration reaction
- Hydroboration
- Reaction with carbenes: cyclopropane synthesis
- Hydroxylation reactions via various reagents; stereochemical outcome
- Ozonolysis
- Alkenes in nature: pheromones

4. Alkynes: The Carbon-Carbon Triple Bond
- Preparation: Double elimination; Alkylation
- Acidity of terminal alkynes
- Reduction of alkynes: catalytic hydrogenation, sodium reduction
- Electrophilic addition to alkynes: halogenation; hydration
- Hydroboration
- Ethynes in nature

5. Delocalized pi Sistems
- Conjugated dienes
- 1,2- versus 1,4-addition
- Diels-Alder cycloaddition

6. Aldehydes and Ketones: the Carbonyl Group
- Preparation of Aldehydes and Ketones
- Nucleophilic Addition reaction: the mechanism
- Addition of water, alcohols, ammonia, and hydrogen cyanide
- Deoxygenation of the carbonyl group
- The Wittig and the Baeyer-Villiger reactions
- Oxidative chemical tests

7. Enols, Enolates, and the Aldol Condensation: alpha,beta-Unsaturated Aldehydes and Ketones
- Acidity of Aldehydes and Ketones: enolate ions
- Keto-enol equilibria
- Halogenation and alkylation
- Aldol condensations
- Conjugate additions to unsaturated Aldehydes and Ketones, Michael addition

8. Carboxylic Acids and Derivatives
- Structure and properties of Carboxylic Acids and Derivatives
- Preparation of Carboxylic Acids
- Substitution at the carboxy carbon: addition-elimination mechanism
- Reduction and bromination reactions
- Relative reactivities of Carboxylic Acid Derivatives (esters, amides, anhydrides, acyl
halides) and their chemistry. Lactones and lactams.
- Nitriles: preparative techniques and properties.

9. Ester Enolates and the Claisen Condensation: Synthesis of beta-Dicarbonyl Compounds
- Claisen condensations
- Beta-Dicarbonyl Compounds as synthetic intermediates

10. Experimental Organic Chemistry

Study-Unit Aims:

This study-unit aims to present the reactions of the most common classes of simple organic compounds as detailed in the study-unit description. Furthermore, students will also be trained to perform organic chemistry experiments and interpret results.

Learning Outcomes:

1. Knowledge & Understanding:

By the end of the study-unit the student will be able to:
- Classify organic compounds in relation to the functional groups present in the molecule and assign the appropriate name to the organic molecules according to IUPAC rules.
- Illustrate the reactivity and the main reaction mechanisms of the common organic functional groups as mentioned in the study-unit description.
- Propose synthetic routes to simple chemical structures.

2. Skills:

By the end of the study-unit the student will be able to:
- Manage information to solve problems.
- Perform organic chemistry experiments safely.
- Check the correctness and reliability of method.
- Interpret correctly and verify the results of organic experiments.
- Discuss results of experimental work in relation to established knowledge.

Main Text/s and any supplementary readings:

Vollhardt, K. Peter C., Schore, Neil E., Organic Chemistry, Structure and Function. [7th ed., 2014] W. H. Freeman & Co. ISBN: 978-1-4641-2027-5.

Sykes P.l., A Guidebook to Mechanisms in Organic Chemistry. (6th ed., 1986) Longman Publishing Group. ISBN: 0-582-44695-3.

Mc Murry J., Organic Chemistry. (7th ed., 2008) Thomson Brooks/Cole. ISBN-13:978-0-4951-1258-7.

ADDITIONAL NOTES Please note that a pass in the Practical component is obligatory for an overall pass mark to be awarded.

STUDY-UNIT TYPE Lecture, Independent Study, Practicum & Tutorial

Assessment Component/s Assessment Due Resit Availability Weighting
Progress Test SEM1 No 10%
Practical [See Add. Notes] SEM1 No 20%
Examination (2 Hours) SEM1 Yes 70%

LECTURER/S David C. Magri

The University makes every effort to ensure that the published Courses Plans, Programmes of Study and Study-Unit information are complete and up-to-date at the time of publication. The University reserves the right to make changes in case errors are detected after publication.
The availability of optional units may be subject to timetabling constraints.
Units not attracting a sufficient number of registrations may be withdrawn without notice.
It should be noted that all the information in the study-unit description above applies to the academic year 2019/0, if study-unit is available during this academic year, and may be subject to change in subsequent years.