CHEM 2120 Midterm 1 Practice

NOMENCLATURE/STRUCTURES
Give proper names/draw the proper structure for the following compounds.

p-bromobenzaldehyde 3-benzyl-2-phenylhepta-1,6-diene

CHEMICAL REACTIONS
Fill in either the reactant/products or reaction conditions required to complete the
following reactions
 NO2

Toluene
+
heat

HN
O

For the next two, draw all possible products and indicate the major one(s).
MECHANISMS

1. Fill in the missing reagents and then draw the mechanism and predict products of
the following:
2. Draw the mechanism for the bromination of:

3. Draw a mechanism for the last reaction in the previous section.

4. Draw the mechanism for the following:

AROMATICITY

1. Draw a π-system (orbital) diagram for:

2. Determine whether the following are non-aromatic, aromatic or anti-aromatic

MOLECULAR ORBITAL THEORY

1. Draw the molecular orbital diagrams for the allyl radical, allyl anion and allyl
cation; include nodes and energy filling diagrams as well as indicating HOMO,
LUMO and SOMO, as appropriate. (As an example, the butadienyl system is
shown.
 2. Draw a Frost Circle for [8]-annulene and use it to determine “aromaticity.”

ENERGETICS

Draw the energy diagram for an SN2 reaction and point out two ways in which the
energy of the transition state can be lowered.