Dr.

Fei Liu CBMS204 workshop

Learning Objectives
The central theme: understanding structure, reactivity, and mechanism as a whole

Important things to remember about a reaction:

Stereochemical principles (regio- and stereo-selectivity, enantioselectivity, diastereoselectivity,
stereospecificity, retention/inversion/racimisation)

Energy considerations (exothermic or endothermic reactions; energy diagram; Hammond

postulate; equilibria; kinetic vs. thermodynamic control)

Kinetic considerations (activation energy barrier; rate equations; isotope effects)

Solvent effects; ion-paring

For the functional groups such as alkenes, alkynes, alkyl halides, and alcohols, recognise,
understand, and reproduce:
the reactivity of the functional group due to its structure and bonding characteristics;

reactions (the reagents and the mechanisms if they have been discussed) for their preparation
(study the functional groups together to see how they inter-convert)

reactions (the reagents, conditions and the mechanisms if they have been discussed) that these
functional groups undergo (study the functional groups together to see how they are related)

key reagents (in addition reactions of alkenes/alkynes; reduction/oxidation of

alkenes/alkynes/alcohols; organometallic reagents; alcohol activating agents)

key mechanisms (radical mechanisms; carbocation rearrangement; addition reaction

mechanisms; E1/E2/SN1/SN2 and their competition) and the associated key
intermediates/transition structures/selectivity issues.

You should be able to summarise whats covered so far according to the headings above. You
must practice drawing mechanisms (arrow pushing).
Dr. Fei Liu CBMS204 workshop

Workshop problems:

I. The following problems are from your textbook (answers in the solutions manual), and some of them
have been given in your lecture notes (alkenes and alkynes) for you to work on. A few of the
following will be discussed in the workshop. Your spot tests will also be discussed.
7.47, 7.48, 7.49, 7.55, 8.26, 8.27, 8.28, 8.33, 8.37, 9.22-9.25, 9.27-29 (alkenes/alkynes)
10.20, 10.27, 10.37, 11.41, 11.42, 11.48, 11.51, 11.68 (alkyl halides)
17.30, 17.39, 17.41, 17.43 (alcohols)

II. Propose a mechanism for the following reaction:

Cl

OH HCl

III. Provide a mechanism (with curved arrows) to explain the formation of 2-bromo-2-methyl-
butane from 3-methyl-1-butene in the presence of HBr.
HBr Br

3-methyl-1-butene 2-bromo-2-methyl-butane

IV. Provide the major product of the reaction below with mechanism:
O

N Br

O
N-bromosuccinamide
CCl4, h!

V. Propose a synthesis for the following using any reactions you deem necessary. Show only the
reagents needed for each reaction and the structure of any intermediates formed with appropriate
stereochemistry if necessary. More than one step may be necessary. No need to provide
mechanisms but make sure you clearly indicate all reagents and any intermediates.
OH