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(Use Answer Sheet For Your Answers) CHM 2210, Wagener October 11, 2010 Progress Test Two/Fall 2010 1. (15 pts) Give the IUPAC name for compounds A and B. In Space C, use a Fischer projection to draw the meso structure for 2,3-dichlorobutane, placing the chlorines at the
top and bottom positions of the structure.
CH3 OWN Compound A Compound B (15 pts) True or False. These questions test your knowledge of concepts. 3) Compound A in Question 1 is chiral.
b) The molecule to the right is chiral.
c) A racemic mixture of enantiomers can be resolved by converting them to meso compounds. d) A reaction intermediate corresponds to an energy maximum between two transition states. e) Cycloheptene can exist as a u'ans achiral diastereomer. (20 pts) Note: a 2 Part Question: A) Consider the reaction shown below. Clearly illustrate
the complete mechanism to explain the product’s formation. Be sure to include all "curvy
arrows" showing the ﬂow of electrons, and be sure to properly assign formal charge as you go through the mechanism. B) Is the product of this reaction a racemic mixture? DO THIS
ON THE ANSWER SHEET. CI
041+ HCl ————> CE (8 pts) Explain in 20 words or less why ethanol (CHaCHZOH) is less acidic than acetic
acid (CH3COOH). DO THIS ON THE ANSWER SHEET. (12 Points)What term most accurately describes the relationship between the following
pairs of compounds? Your choices are: A) Enantiomers B) Identical Compounds
C) (EZ) isomers D) Conformers E) Different Compounds F) Meso Compounds G) Constitutional Isomers. WRITE THE LETTER FOR YOUR ANSWER ON THE
ANSWER SHEET. H Br CH3 OH
H CH3 0”
53) CH3 Br H Br 5b) HO
H CH3 (TURN THIS PAGE OVER) (Continued) 5c) (15 Pts) Draw the structure of the major product for the following reactions. If no
reaction occurs, write "No RXN". If stereochemistry is important in your answer, then
write a word or two regarding the stereochemical outcome (ie, enantioselective chemistry, pure enantiomer, racemic mixture, meso compounds formed, no stereocenter,
etc). DO THIS ON THE ANSWER SHEET. 6a) + HCl ___, 1. Hg(OAc)2, H20 W 6b) 2. NaBH4
3 1)Br2, H20
60) DMSO (10 pts) Select the most stable reaction intermediate below. In 10 words or less, explain
why it is the most stable structure. DO THIS ON THE ANSWER SHEET. TAG TAG TAc
H9 59!. H9
+ \ ‘ . C’ib <—> / +
\\\\"C -—C "’11, ““7 v,” \\\‘..C —C ”’0,
H‘ I \ /H H H H‘ l \ ’H
R H R H R H (5 pts) Can n (pl) electrons act as a Bronsted—Lowry Base? Answer yes or no, then in 10
words or less, explain why. DO THIS ON THE ANSWER SHEET. ...
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- Fall '01
- Organic chemistry