Chemistry 3140 -- Klavetter KEY

Exam 1: 150 pts (10 pts each)

1. Provide an IUPAC name for each of the following compounds. Be careful to correctly
include any appropriate dashes, commas, spaces in the name.

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2. Draw the most stable Newman projection for 3-methylpentane, as viewed along the
C2-C3 bond axis (C2 is the front carbon, C3 is the rear carbon).

3. Draw the bond line formula for (CH3CH2CH2)3COH.

4. Draw all isomers having the molecular formula C3H9N

5. In the molecule CH2O, which orbital(s) overlap to form

a. the C-O pi bond? _____________________

b. the C-H sigma bond? ________________________

6. How many sigma bonds are in HOCH2CH=CHCH2CH2NH2? ______________

7. Draw any molecule that could be classified as an ester, then draw a resonance
structure for it.

8. Give the IUPAC name for the following molecule

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9. Draw the gauche conformation for HOCH2CH2OH. Then explain why it is more
stable than the anti conformation.

10. Draw the most stable conformation for cis-1,2-dichlorocyclohexane. How many
hydrogen atoms are in axial positions for this molecule?
11. Draw all important resonance forms for CH2CHOCHCH2

12. Draw the three most stable resonance forms for H2NCO2H. Label these structures
as “most stable”, “second-most stable”, and “third-most stable” (from greatest
stability to least stability).

13. Draw the products which form upon proton transfer between the following species:
14. Which of the following species is more acidic, and why? (explain why, or no credit)

15. a.) Define “molecular orbital” using a complete sentence.

b.) Define “hybrid orbital” using a complete sentence.