1. a) For each section below, choose the arrows that best describe the relationship between
the right hand side and left hand side of the equation by putting a letter in the central boxes.
A B C D E
OH + N Na+ O Na+ + NH
iii) CH3 CH3
H CH3 H H
NH O NH O
NH NH2 NH2 NH
b) Name the functional groups circled in the molecule shown below.
c) Redraw compound 1, clearly showing it in its most stable conformation. If more than
one structure is drawn please circle your final answer.
d). Draw the meso form of 2,3-dibromobutane using the template below. Indicate the
absolute configuration at each stereogenic center as being either (R) or (S).
2. a) Name the following compounds using IUPAC nomenclature, including as necessary
designation of stereochemistry.
b) Draw all of the stereoisomers of 1,2,3-trichlorocyclopentane (note substitution pattern!).
Start with the template below and redraw as necessary. Draw each isomer only once and
show stereochemistry where appropriate using "wedges" and "dashes".
c). Draw two resonance structures that contribute most to the overall picture of nitromethane
(CH3NO2). In each structure, clearly show all lone pairs and formal charges.
3. a) Draw a transition state for the following reaction in the box below. Clearly show the
Br + NH3 NH3 + Br
b) Treatment of Compound 1 with methanethiolate (CH3S-) gave a single isomer of
compound 2. Draw a mechanism for the reaction (no transition state(s) required),
and clearly show the structure and stereochemistry of compound 2.
O CH3S Na
c) Draw a detailed mechanism for the reaction shown below. It is not necessary to
show any transition states.
H + HO O
d) Which compound is present in a greater amount at equilibrium, 3 or 4?
Briefly explain your reasoning.