Test 1
Dr. Bachrach
CHEM 2319-2
2/11/08

1) Provide the IUPAC name for the following compounds.

a)

(3Z)-3,6-dimethyl-4-propyl-3-heptene

b)

Cis-1-sec-­butyl-3-ethylcyclohexane

c)

5-cyclopropyl-3,7-dimethyl-1-octene

2) Draw the structure of 1,3-dimethyl-1,3-dipentylcycloheptane.

3) Indicate the value of each of the C-C-C bond angles about each of the bold carbon atoms

04) Draw the Lewis dot structures of the following compounds:

a)

You needed to draw at least three of these for full credit.

b)

5) Consider the sugar glucose below. The six member oxygen-containing ring adopts a geometry just like that of cyclohexane. There are many other possible sugar molecules that differ from glucose in the arrangements of the OH and CH2OH groups – their relative cis and trans arrangements. Why do you think that glucose is the most widely found sugar in nature.? Justify your answer.

So, the most stable conformation of glucose has all of the substituents in the equatorial positions, which means they are all far from each other and there are no 1,3-diaxial interactions (except between the very small H atoms). This is a very stable structure. Now, any other sugar must place one or more of these substituents into an axial position, and so these sugars will be less stable! Nature has chosen to utilize the most energetically stable sugar!

6) Assign the charge distribution to this neutral molecule.

FC(X) = #velnce e^- - # bonds - # unshared e^-

FC(O₁) = 6 -2 -4 = 0

FC(O₂) = 6 -2 -4 = 0

FC(O₃) = 6 -2 -4 = 0

FC(O₄) = 6 -1 -6 = -1

FC(S) = 6 -6 -0 = 0

FC(N) = 5 -4 -0 = +1

For all C: FC(C ) = 4- 4 – 0 = 0

For all H: FC(H)= 1 – 1 – 0 = 0

7) Draw the Newman projection for the three staggered conformations of 3‑chloro-4-ethylhexane looking down the C₃-C₄ bond.

8) Draw and name all of the acyclic alkenes with molecular formula C₅H_8.