Reactivity and Mechanism


Unit code: CHEM10412
Credit Rating: 10
Unit level: Level 1
Teaching period(s): Semester 2
Offered by School of Chemistry
Available as a free choice unit?: N

Requisites

Prerequisite

Aims

Provide an introduction to organic chemistry and develop a solid understanding of mechanisms

Overview

Carbonyl Group Chemistry (Dr John M Gardiner, 7 lectures)

  • Structure of the carbonyl group and review of nucleophilic additions to aldehydes and ketones
  • hydration and hemiacetal formation
  • substitution at carbonyl groups leaving groups and use of pKa as a guide to the breakdown of tetrahedral intermediates
  • substitution reactions of acid chlorides
  • interconversion of carboxylic acids, esters, acid chlorides and amides
  • synthesis of alcohols and ketones from carboxylic acid derivatives - reactions with organometallics
  • acid and base catalysis
  • substitution in which carbonyl oxygen is lost formation and hydrolysis of acetals and imines, protecting groups, reductive amination, the Wittig reaction.
  • introduction to simple enol and enolate chemistry

Substitution and elimination at saturated carbon (Professor Igor Larrosa, 7 lectures)

  • SN2 reactions nature of the transition state, relative reactivity of different substrates and reagents
  • hard and soft acids (electrophiles) and bases (nucleophiles)
  • reactivities of different leaving groups halides and p-toluenesulfonates
  • SN1 reactions structure and stability of carbocations, relative reactivity of different substrates
  • stereochemical aspects of SN1 and SN2 reactions
  • E1 and E2 reactions kinetics, substrate structure dependence, base and leaving group
  • competing substitution and elimination

Reactions at Unsaturated carbon in alkenes and arenes (Professor David J Procter, 7 lectures)

  • addition of bromine to alkenes - bromonium ions, regioselectivity of opening, effect of nucleophilic solvents
  • epoxides and epoxide opening
  • other oxidations of alkenes
  • Markovnikov and anti-Markovnikov hydration of alkenes
  • hydrogenation of alkenes to give alkanes
  • reduction of alkynes
  • structural features and reactivity of benzene (and other aromatics)
  • nitration, sulfonation, halogenation and Friedel-Crafts reactions of benzene
  • direction and activation in substituted benzenes
  • diazotisation
  • nucleophilic aromatic substitution

Workshops (Dr. Gardiner, Prof. Larrosa, Prof. Procter, 3 workshops)

  • carbonyl group chemistry
  • substitution and elimination at saturated carbon
  • reactions at unsaturated carbon in alkenes and arenes

Learning outcomes

  • To predict the outcome of reactions at sp2 centres in terms of interaction of orbitals.
  • To apply knowledge of structure and bonding to rationalise the mechanism of reactions at sp2 centres.
  • To introduce organic reactivity in the context of CHEM10101.
  • To provide a grounding in basic mechanistic organic chemistry, to include orbital description of reactions and basic stereoelectronics (continuity from “shape” in CHEM10101).
  • To emphasise interdisciplinary aspects (to run synchronously with kinetics in CHEM10212).
  • To predict the outcome of reactions at sp2 centres in terms of interaction of orbitals.
  • To apply knowledge of structure and bonding to rationalise the mechanism of reactions at sp2 centres.
  • To define the concept of aromaticity and use it to rationalise and predict reactivity of arenes.

Transferable skills and personal qualities

Students will be expected to  use material covered in lectures or tutorials to independently search different text sources to support their understanding and thus encourage and reinforce investigative skills. The course contains in-lecture problems and the tutorials are problem-based ensuring students can illustrate core understanding but the problem-solving skills involved will also include challenging problems designed to develop and advance their analytical skills in bringing different concepts to bear on unseen problems. The tutorials in support of this course material also provide facility for student to develop communication skills through group discussions of problems and reporting on the own work in a group setting.

Assessment methods

  • Written exam - 100%

Recommended reading

J Clayden, N Greeves, S Warren, Organic Chemistry, 2nd edition, OUP, 2012

Feedback methods

  • Students will be expected to submit tutorial problem sheets that will be marked and discussed in three-weekly tutorials.
  • Revision lectures and problem sessions will be held during and/or at the beginning of each teaching block.
  • Three workshops will be held at the end of the teaching session.
  • Online quizzes will be provided once a week.

Study hours

  • Assessment written exam - 2 hours
  • Lectures - 21 hours
  • Practical classes & workshops - 3 hours
  • Tutorials - 3 hours
  • Independent study hours - 71 hours

Teaching staff

John Gardiner - Unit coordinator

David Procter - Unit coordinator

Igor Larrosa - Unit coordinator

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