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CHEMISTRY 3331
SECOND EXAM
Dr. Olafs Daugulis
27 March, 2015
Name______________________________________
(print, legibly)
Last
First
Last 4 digits of student number ___________________
SEAT NUMBER_______________________________
Please read all directions carefully. Write all answers legibly in the appropriate
spaces and THINK about what you are doing. Give only ONE answer for each
question (100 pts total).
1. (16 pts) Carefully draw the structure of the compound whose name is given. Be sure to
indicate stereochemistry where appropriate:
Et is up
(on wedge)
stereochem 1pt
ring 1 pt
substituents 2pts
db stereochem 1 pt
substituents 2 pts
chain 1 pt
ring 1 pt
cis 1 pt
vinly 2 pts
ring 1 pt
double bonds 2 pts
substituents 1 pt
2. (17 pts) The reaction show below gives three major products. Draw a complete mechanism to
explain the formation of these three products, using arrows to indicate the flow of electrons. Be
sure to show all intermediates and clearly indicate any charges. Do not draw transition states
(dotted bonds). 6-74b – HOMEWORK!!!
each step 2 pts except loss of Br (3 pts)and resonance (4 pts)
3. (12 pts) Ethylcyclopentane shown below can be monobrominated to give seven different
products.
(a) Draw the structure of two ACHIRAL products in the boxes provided.
(b) Circle the product that is the most reactive in E1 reaction.
(c) Put a star next to the product that is most reactive in E2 reaction.
4 pts ea structure
2 pts ea circling/star
4. (12 pts) Starting from CYCLOHEXANE and any inorganic reagents, outline the synthesis of
the molecule shown below. Show intermediates and reagents.
3 pts each step
5. (12 pts) Molecule shown below is Adderall XR, a bestselling psychostimulant by Shire
Pharmaceuticals. It is sold also as Dextroamphetamine by Teva. For the Fischer structure shown
below, in the empty box on the left indicate the absolute configuration of the indicated chiral
center. On the partially complete skeleton drawn on the right add the required substituents to
give the exact same molecular configuration. On the structure below, add the required
substituents to give the opposite configuration.
4 pts ea
Fun Facts: (1) it is believed that up to 30% of college students use Adderall non-medically. The
numbers vary significantly by school, with the greatest proportion of users at private and "elite"
universities. Link: http://www.ncbi.nlm.nih.gov/pubmed/18980888.
(2) During World War II, Adderall (then called amphetamine) was used extensively by both the
Allied and Axis special forces for their stimulant and performance-enhancing effects.
(3) Enantiomers of Adderall have different activity in humans, with one enantiomer being two to
three times more active than the other enantiomer.
(4) It can be fatal to humans with heart disease.
6. (25 pts) For each of the reactions shown below, draw the structure of the major organic
product(s) or starting material. Give only one structure per box and indicate stereochemistry
where applicable.
-2 pts for wrong stereochem
-1 pt wrong db isomer
-2 pts substitution
correct also if draw 2 enantiomers of 1st product
5 pts ea
7. (6 pts) ROADMAP. Put the product of each reaction sequence or necessary reagents to
accomplish the transformation in boxes provided.
3 pts ea structure
For extra-special extra credit 5 points above 100 please write the trivial name of the compound
or the plant in which the product of these transformations can be found in the box below:
nicotine, or tobacco for full credit
3 pts if write potato,
tomato, eggplant, pepper,
nightshade
END OF EXAM – NOTHING BELOW THIS WILL BE GRADED