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Elementary Organic Chemistry
CHE 220
Exam 2
February 25, 2002
Dr. R.W. Nagorski
A person ceases to be a beginner in any given science and becomes a master in that science when they
realize that they are going to be a beginner all their life.
R.G. Collingwood (1889-1943)
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Name:___________________
ID#:_____________________
CHE 220 – Exam 2 Page 2 February 25, 2002
Part A: Nomenclature
Give the IUPAC names for the structures shown below. (6 points)
Given the IUPAC names below; draw the structure for each compound. (6 points)
Part B: Conceptual Problems
- Indicate whether the following compounds are chiral or achiral. (6 points)
a)
b)
Br H
Cl OH
a) (S)-3,3-diethyl-5,5-dimethylcyclohexanol
b) 4-chloro-3,5-diiodo-2-methyl-4-propylnonane
CH 3
H 3 C
CH 3
CH 3 H
Br CH^3
CH 3
CHE 220 – Exam 2 Page 4 February 25, 2002
Determine the stereochemistry at all of the stereocenters in the compounds shown below. (5 points)
Would you characterize the sugar below as a hexose or a pentose? (2 points)
Is the structure shown below a monosaccharide, disaccharide, or polysaccharide? (2 points)
CH 3 Cl Br CH 2 CH 2 CH (^3) H (^) H
Cl
H
CH 3 CH 2 Cl H 3 C OH
HO H
H OH
HO H
H OH
H OH
CH 2 OH
O
O
HO
OH
O
HO
OH
OH
O
HOH 2 C
HO CH 2 OH
CHE 220 – Exam 2 Name:_______________________ Page 5 February 25, 2002
Rank the following compounds from most acidic to least acidic. (8 points)
Three types of organometallic bonds were discussed in class. Rank them from most reactive to least reactive ( points)
Give two characteristics of an SN2 reaction that an SN1 reaction does not possess? (4 points)
Rank the oxidation states of methane from least to most oxidized. (5 points)
a)
b)
OH OH
OH OH
Cl Cl
H
Cl Cl Cl (^) Cl
HI (^) HCl HF (^) HBr
Associated Ionic Dissociated Ionic Polar Covalent
CH 4 CH 3 OH
O
H H
O
H OH
O
HO OH
CHE 220 – Exam 2 Name:_______________________ Page 7 February 25, 2002
- What is the major product or products for each of the following reactions shown below? (24 points)
I H
+ HO-
OH
OH PCC
H 2 CrO (^4)
CH 3
OH (^) SOCl 2
Cl (^) + - CN
OH
+ HI
Cl (^) + 2Li
a)
b)
c)
d)
e)
f)
g)
h)
CH 3
H OH
CHE 220 - Exam 2 Page 8 February 25, 2002
- Give a brief definition for each of the following words. (9 points)
a) Aprotic Solvent:
b) Diastereomer:
c) Disaccharide:
Bonus Questions: (Bonus questions are graded correct or incorrect. No partial credit is given)
What is the name of the instrument used to measure the optical rotation of a plane of polarized for an enantiomerically pure compound? (3 points)
What do the letters of the acronym IUPAC stand for? (3 points)
