Exam # 2 Chemistry 208 Spring 2016

Your name:___________________
Laboratory Section:___________

Exam # 2
Chemistry 208, Organic Chemistry I
Spring 2016
With

Dr. Bell
Exam # 2 Chemistry 208 Spring 2016

1) (15 pts) Please provide a structure for the following names:

A. Chloromethoxymethane

B. Diethyl ether

C. Hydroquinone

2) (15 pts) Please provide either the IUPAC or common name for the following structures:
 Exam # 2 Chemistry 208 Spring 2016

3) (30 pts.) Predict the products from the following reactions:

Exam # 2 Chemistry 208 Spring 2016

4) (14 pts) Predict the product of the following reaction. (Show stereochemistry):

5) (16 pts) What Diene and Dienophile would react to give the following Diels-Alders Products?
Exam # 2 Chemistry 208 Spring 2016

6) (10 pts) Lable the following compounds as either aromatic, antiaromatic or nonaromatic:

7) ( 10 pts) Both pyrrole and pyridine are aromatic compounds. Explain why pyrrole (pKb = 13.6)is a
much weaker base than pyridine (pKb = 8.8).

8) (10 pts) Please use the polygon rule (a.k.a. “Frost” circle) to draw the relative energy levels of the
Molecular orbitals of cyclopentadiene anion.
Exam # 2 Chemistry 208 Spring 2016

9) ( 15 pts) Explain why an electron donating groups such as methoxide directs incoming electrophiles
to attach either the position ortho or para positions on the ring and not the meta position. Please
uses resonance forms to help explain your answer

10) (15 pts) Starting from benzene, arrange the following reaction is an sequence that will produce the
following target compound. You may not need all af the reactions to complete this task: