ORGANIC CHEMISTRY EXAM

1

Organic Chemistry Exam III Chapter 4

Open Book Name:___________________ Submission Instructions:

• Exams are to be submitted to Canvas Assignments > Exam III TakeHome • This exam is due on 11/13/20 at 10:45AM • No late submissions will be accepted • Exams are to be submitted in one orderly PDF file, all other formats will not be accepted • Only one upload permitted • Submissions in which pages are out of order will incur a 10 % penalty • All work must be shown for credit/partial credit

Short Answers:

1. List the substituents shown below in order of relative priority from greatest to smallest.

-OH, -COOH, -CH3, -C=CHCH2CH3, -CH=CH2

2. Using IUPAC nomenclature and syntax, name the compound shown below. Include in the compound’s name the Z or E configuration.

3. Does the following compound have a R or S configuration and why?

2

4. How would the compound shown below affect plane polarized light?

5. A solution containing 5.0g of compound dissolved in 1000mL of solvent generated an observed rotation of plane-polarized light (λ = 589.6nm) of 27° in a polarimeter tube 250mm long at a temperature of 25°C. What is the specific rotation of the compound?

6. How many asymmetric centers does the compound shown below have?

3

7. Are the molecules shown below enantiomers, diastereomers, constitutional isomers, or identical?

8. Using IUPAC nomenclature and syntax, name the compound shown below. Include in the compound’s name the Z or E configuration.

9. Are the molecules shown below enantiomers, diastereomers, constitutional isomers, or identical?

4

10. Are the molecules shown below enantiomers, diastereomers, constitutional isomers, or identical?