1. Demonstrate an understanding of the major reaction pathways and mechanisms in organic chemistry. KNOWLEDGE AND UNDERSTANDING
LEARNING

2. Apply knowledge of the theoretical aspects of organic chemistry to understanding and predicting reaction pathways and their outcomes
ANALYSIS
PROBLEM SOLVING

3. Ability to effectively search the scientific literature to locate sources of information and incorporate these into written reports
ENQUIRY
COMMUNICATION
REFLECTION.

4. Complete practical exercises and demonstrate an appreciation of the scope and limitations of the results obtained.
SS2

Students will study organic reaction mechanisms using the curly arrow notation and develop an appreciation of the relative stabilities and reactivities of reactive intermediates (carbenium ions, carbanions, radicals and carbenes).

The SN1, SN2, E1, E2 and E1CB mechanisms are developed further through consideration of solvent effects, basicity and nucleophilicity, and steric and electronic effects of substrate structure on rates of reaction. Neighbouring group effects and their influence on rearrangements with a particular emphasis on steric requirements. Basic radical and carbene chemistry. Stability of carbanions is particularly developed in in the context of enolate chemistry including condensation and cyclisation reactions.

Electrophilic addition to p-systems, regioselectivity and stereoselectivity with alkenes and 1,3-dialkenes, including kinetic vs thermodynamic control. Electrophilic aromatic substitution of benzene derivatives, mechanisms and substituent effects, regioselectivity in multiple substitution reactions.

Chemistry of enols and enolates – enolization, acid-base and pKa, enols as reactive intermediates, their structure, stability and methods of formation, regioselectivity, enolate alkylation, aldol addition and condensation, Claisen and Dieckmann condensation, mannich reaction.

Organometallic reagents for C-C bond formation – Grignard reagents, their formation and reactions with water, alcohols and alkynes.

Practical exercises will include multi-step synthetic procedures for the preparation of a range of organic compounds, their purification by a range of methods including distillation and recrystallization, and subsequent characterisation.

Students will complete 3 elements of assessment for this module:

1. EXAMINATION 1(at the end of Semester 1), 1.5 hour worth 25% of the module (learning outcomes 1and 2)

2. PRACTICAL PORTFOLIO, worth 50% of the module (learning outcomes 2, 3 and 4)

This will include a laboratory notebook, written reports of experiments, a reflective summary of knowledge and skills development (learning outcome 3)

3. EXAMINATION 2 (at the end of semester 2), 1.5 hour worth 25% of the module – FINAL (learning outcomes 1and 2)

4. Formative assessment: Students will be provided with formative assessment and feedback via practical classes, reports, and tutorial sessions and specimen exam/test questions. (all learning outcomes)

Each week there will be a 2-hour interactive lecture / seminar during which students will be introduced to core material and develop their understanding through problem-solving exercises undertaken in class = 48 hours.

There will be 16 x 3 hour practical sessions during which students will develop their practical and experimental skills through undertaking a number of laboratory-based exercises that also develop the theoretical aspects of the module = 48 hours.

Each experiment is preceded by a pre-laboratory exercise that involves a combination of audio visual resources, accessible via Blackboard, that helps students prepare for the practical work, with a short formative quiz based on the content to be completed before starting the relevant practical task. It is anticipated that students will spend 2 hours on each of these activities = 32 hours.

The remaining 172 hours of independent study will be used to research background information related to the delivery of the core material and to build the practical portfolio.

Housecroft and Constable (2010), Chemistry,4th Ed, Prentice Hall

Clayden, Greeves and Warren (2012), Organic Chemistry, 2nd Ed, OUP Oxford

Levy (2017), Arrow-Pushing in Organic Chemistry, 2ed Ed, Wiley