Chem 212Survey of Organic and BiochemistryFall 2006

______

Print your full name legibly in the space above.

Exam 1: Ch. 1-5

28 September 2006

Instructions:

1. If you leave the room for any reason you may not return to continue the exam.

2. No books, notes, or calculator of any kind are permitted (including cell phones.)You may borrow a model kit.

3. Put all your answers on this exam paper. If you want something graded which is written on scratch paper, you must indicate so in the regular space for the answer.

Good Luck!

  1. (6 pts) Draw a reasonable Lewis structure for each of the following, showing all lone pairs and formal charges where relevant:
  2. P2
  1. NO (an important neurotransmitter)
  1. CH3O- (carbon is the central atom)
  1. (6 pts) State whether the structures in each pair below are the same molecule, cis-trans isomers, constitutional isomers, or not related.
  1. (17 pts) Answer the following questions about the structure below, which is Norethindrone, one component of the birth control pill.
  1. How many carbon atoms are in the structure? ______
  1. What is the degree of hydrogen deficiency (unsaturation) of the structure? ______
  1. How many hydrogen atoms are in the structure? ______
  1. On the structure above, indicate with an arrow one bond that can freely rotate around 360°. Do not point to an atom!!!!!!
  1. Circle and name three functional groups in the structure above.
  1. Use the VSEPR method to predict the geometry around each of the following atoms (linear, triangular planar, triangular planar/bent, tetrahedral, tetrahedral/triangular pyramidal, tetrahedral/bent, triangular bipyramidal, octahedral, octahedral/square planar)

a ______d ______

b ______e ______

c ______f ______

  1. Give approximations for the angles around each of the numbered atoms in Lipitor:

1 3

2 4

4. (3 pts) Drawa Newman projectionfor a staggered conformation of 2,2-dichloropentane looking along the C2-C3 bond:

5. (12 pts) Give the chemical name for the following molecules:

6. (12 pts) Next to each name, draw the correct line-bond structure:

2-isopropyl-5-methyl-cyclohexanol

trans-1,4-cyclohexanediol

1-chloro-2-propanol

m-bromostyrene

3-methylcyclohexene

3-cis-5-cis-2,4-dimethyl-3,5-decadiene

7. (12 pts) For each example, draw two different line angle structures:

  1. C10H14, with an aromatic ring (may have other functional groups as well) Draw two different structures!
  1. C7H14O2, with a carboxylic acid (may have other functional groups as well) Draw two different structures!
  1. C5H8O with a ketone (may have other functional groups as well) Draw two different structures!

8. (20 pts) Draw the structure of the organic products for each of the following reactions

.

9. (3 pts) The structure below represents the molecule capsaicin, which is the ingredient in hot pepper which gives it the hot flavor and burning sensation. Based on the structure of capsaicin, do you think it would be more soluble in water or hexane? Explain your answer.

10. (3 pts) Circle the isoprene units in lycopene, the red pigment in tomatoes which some believe protects the prostate:

11. (3 pts) A new type of anti-cancer drug currently under development is called an “endiyne” anti-cancer drugs. Based on this name, what structural features are present in the molecule?

12. (3 pts) The structure below represents vitamin K. Below it, draw the reduced form of Vitamin K.

Page 1