Chemistry 2080 / Professor Smith

Homework for Chapter 17

The problem is worth 4 points
Directions:
You may work solo or with one (and only one) study partner.
If working with a partner:
o Do this assignment by yourself first.
o Only after that, consult with your study partner.
o Come to a consensus on your answers.
Submit one response with one (working solo) or both (working with a partner) name(s) on it.
Consult with no one else (except me if needed).

Due Monday 4/7
It turns out it is fairly straightforward to detect aromaticity by NMR spectrometry. The outside ring
protons attached to multiple bonds on aromatic compounds have higher chemical shift values than outside
ring protons on non-aromatic conjugated alkenes. Based on the discussion of aromaticity in the text, explain,
using structural features, why the outside ring protons in compound A have higher observed chemical shifts
than the outside ring protons in compound B.

.

Due Friday 4/11
a. Draw the mechanism for the reaction that makes 4-methylethylbenzeme from ethylbenzene.

b. Draw all of the reasonable resonance forms for the carbocation intermediate in the mechanism for part
a.

c. Draw a circle around the most stable resonance form.

Due Monday 4/14
a. Show all of the reactants and organic products for each reaction in the synthesis of 3-chloronitrobenene.

b. Using the same reagents and reactions, design a synthesis of 4-chloronitrobenzene.


Due Wednesday 4/16
Consider1-bromo-1-phenylmethane and 2-bromo-1-phenylethane.

a. Which would react faster with methanol in a nucleophilic substitution reaction?

b. Draw the mechanism of the faster reaction.

c. Using benzene, simple alcohols of fewer than 5 carbons, and any inorganic reagents, show the
reactants and organic products for all reactions in an efficient synthesis of 1-bromo-1-phenylmethane.