Organic Chemistry - Problems

Topics: Stereochemistry, Enantiomer, Chirality Pages: 3 (557 words) Published: June 23, 2013
ORGANIC CHEMISTRY - PROBLEMS

Problem 1.1: Determine whether the two structures in each of the following pairs represent constitutional isomers, different conformations of the same compound, or stereoisomers that cannot be interconverted by rotation about single bonds.

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Problem 1.2: According to Cahn-Ingold-Prelog priority rules, choose the correct order of precedence. A. (Br > (OH > (C(CH > (CH=CH2 > (COOH > (CH2COOH > (CH3
B. (Br > (OH > (COOH > (C(CH > (CH=CH2 > (CH2COOH > (CH3
C. (OH > (COOH > (Br > (C(CH > (CH=CH2 > (CH2COOH > (CH3
D. (Br > (OH > (COOH > (CH2COOH > (C(CH > (CH=CH2 > (CH3

Problem 1.3: Determine the configuration of each of the following alkenes as Z or E as appropriate.

[pic]

Problem 1.4: Determine the configuration of the following alkene. [pic]
A. (2Z,6Z)B. (2E,6E)C. (Z)D. (E)

Problem 1.5: Determine the configuration of the following alkene. [pic]
A. (2Z,6E) hay 2-cis,6-transB. (2E,6Z) hay 2-trans,6-cis C. (2Z,6E)D. (2E,6Z)

Problem 1.6: Examine the following for stereogenic centers.
[pic]
[pic]

Problem 1.7: Cholesterol, when isolated from natural sources, is obtained as a single enantiomer. The observed rotation ( of a 0.3-g sample of cholesterol in 15 mL of chloroform solution contained in a 10-cm polarimeter tube is (0.78°. Calculate the specific rotation of cholesterol.

Problem 1.8:
(a) An aqueous solution containing 10 g of optically pure fructose was diluted to 500 mL with water and placed in a polarimeter tube 20 cm long. The measured rotation was (5.20°. Calculate the specific rotation of fructose. (b) If this solution were mixed with 500 mL of a solution containing 5 g of racemic fructose, what would be the specific rotation of the resulting fructose mixture? What would be its optical purity?

Problem 1.9: Assign absolute configurations as R or S to each of the following compounds. [pic]

Problem 1.10: Write Fischer projections for each of the compounds of...
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