School of Chemistry
Aims and Objectives: Session 2015-2016
Module CH2201: A First Course in Organic Chemistry
Duration:
33 hours
Lecturers:
Dr H. Mitchell and Professor D. Philp*
(*Module Convenor)
Aims:
To introduce students to organic chemistry emphasising the importance of
stereochemistry and mechanism in the reactions of simple monofunctional aliphatic compounds and, in seminar sessions, develop an
understanding of the chemistry of alkanes, cycloalkanes, alkenes, alkynes,
haloalkanes and alcohols.
Objectives:
1.
Appreciate the uniqueness of carbon in its ability to bond to other carbon
atoms.
2.
Understand hybridisation of carbon in alkanes.
3.
Use IUPAC nomenclature for alkanes and define constitutional isomerism
and homologous series.
4.
Understand the use of spectroscopy in structure determination:
a.
Use of infrared spectroscopy to identify functional groups
b.
Use of 1H (number of signals, chemical shift, integration values &
multiplicity) and 13C NMR (number of signals & chemical shift)
spectroscopy to distinguish between constitutional isomers and
identify products of familiar reaction types
5.
Understand the conformations of ethane and butane, relate these to
conformations of cyclohexane and substituted cyclohexanes and be able to
extend these ideas to polycyclic molecules.
6.
Appreciate the strain in, and therefore the reactivity of, cyclopropane.
7.
Understand the reactivity of alkanes towards free radicals, the steps in
chlorination of simple alkanes and the greater regioselectivity of
bromination.
8.
Understand the concept of a functional group, be able to list singlybonded functional groups, Cl–, Br–, I–, HO–, RO–, HS–, RS–, H2N–.
R2N– and use IUPAC rules to name simple examples.
9.
Understand and recognize multiply-bonded functional groups,
C=C
, –C ≡ C–,
simple examples.
C = O etc, use IUPAC rules to name
10.
Define the terms chirality, stereogenic centre and enantiomer and be able
to designate, using Cahn-Ingold-Prelog rules, chirality centres as R or S.
11.
Understand the consequences of having multiple chirality centres in a
molecule and define the term diastereoisomer.
12.
Understand the role of hydrogen bonding in organic chemistry, including
its effect on the boiling point and solubility of alcohols and amines.
13.
Appreciate the relative acidities of a range of organic molecules and how
structural features, including resonance, inductive effects and bond
lengths, can affect the acid / base strength of organic molecules.
14.
Define the terms nucleophile and electrophile, understand the result of
nucleophilic substitution of haloalkanes and describe the reactions using
the conventional 'curved arrow' notation.
15.
Understand the mechanisms of nucleophilic substitution of haloalkanes,
SN1, SN2.
16.
Understand how trends in acidity / basicity relate to those in
nucleophilicity / electrophilicity.
17.
Understand that ß - elimination and substitution reactions can compete
when nucleophiles react with haloalkanes and understand the mechanisms
of ß - elimination reactions and the stereochemical consequences of
substitution (SN1 and SN2) and of elimination reactions.
18.
Understand the influence of the structure of the alkyl group, the nature of
the leaving group, the reagent and the solvent on substitution and
elimination reactions.
19.
Understand that organometallic reagents are formed when metals such as
Li and Mg react with haloalkanes, and that these reagents act as
nucleophiles.
20.
Appreciate the reactivity of allylic halides, the unreactivity of aryl halides
and reactions involving allylic Grignard reactions.
21.
Understand that amines are basic and react as nucleophiles and how
primary, secondary and tertiary amines are formed.
22.
Appreciate the reactions of alcohols – substitution, elimination,
esterification, and oxidation – and know how formation of derivatives can
modify their reactivity in substitution and elimination reactions.
23.
Know reactions for the formation of ethers, including epoxides and other
cyclic ethers.
24.
Understand the relative lack of reactivity of ethers and the reactivity of
epoxides.
25.
Understand the reactions of thiols – acidity, nucleophilicity and oxidation
and know that thioethers are oxidised to sulfoxides and sulfones.
26.
Understand the structure, bonding and isomerism of alkenes.
27.
Understand the stereoisomerism in but-2-ene and designate the
stereoisomers of alkenes as E and Z using the Cahn-Ingold-Prelog rules.
28.
Appreciate the relative stabilities of alkenes.
29.
Understand the reactivity of alkenes, especially the addition of
electrophiles, and use of the "curved arrow" notation to show the
movement of electrons in reactions.
30.
Appreciate the relative stabilities of carbocations and so understand the
orientation of addition of electrophiles such as HCl to propene and to
other unsymmetrical alkenes.
31.
Understand that addition of bromine to alkenes is trans whereas catalytic
hydrogenation is a cis addition.
32.
Understand the mechanism, stereochemistry and synthetic potential of
hydroboration and dihydroxylation of alkenes.
33.
Understand that, under different reaction conditions, addition of HBr to
propene can result in the formation of either 2-bromopropane or
1-bromopropane.
34.
Understand carbocation rearrangements and their role in Wagner Meerwein and pinacol rearrangements.
35.
Appreciate that α-elimination gives rise to carbenes and understand the
role of carbenes and carbenoids in the formation of cyclopropanes.
36.
Identify the result of addition of electrophiles to, and the catalytic
hydrogenation of, alkynes.
37.
Understand keto-enol tautomerism.
38.
Appreciate that the hydrogen on C-1 of alk-1-ynes is acidic, and hence
appreciate their application in synthesis.
39.
Be aware of the idea of retrosynthetic analysis and be able to propose
synthetic routes involving more than one step.