Chem212

SurveyofOrganicandBiochemistry

Fall2006

_______tt______________________
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: a. P2

b. NO (an important neurotransmitter)

c. CH3O- (carbon is the central atom)

2. (6 pts) State whether the structures in each pair below are the same molecule, cis-trans isomers, constitutional isomers, or not related.
H3C H3C H3C CH3 CH3

CH3

CH3

Br

Br

H3C H3C CH3

H3C H3C CH3 Cl

Cl Cl Cl

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Chem212

SurveyofOrganicandBiochemistry

Fall2006

3. (17 pts) Answer the following questions about the structure below, which is Norethindrone, one component of the birth control pill.
a 3 2 1 e d c f b 4 OH

a. How many carbon atoms are in the structure? ___________ b. What is the degree of hydrogen deficiency (unsaturation) of the structure? __________ c. How many hydrogen atoms are in the structure? __________ d. On the structure above, indicate with an arrow one bond that can freely rotate around 360. Do not point to an atom!!!!!! e. Circle and name three functional groups in the structure above. f. 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 b c ____________ ____________ ____________ d e f ____________ ____________ ____________

g. Give approximations for the angles around each of the numbered atoms in Lipitor: 1 2 3 4

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

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Chem212

SurveyofOrganicandBiochemistry

Fall2006

5. (12 pts) Give the chemical name for the following molecules:
H3C OCH 3

Cl

CH3 CH3

HO

HO O

CH3

OH

CH3 H3C H3C

H3C Br CH3

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Chem212

SurveyofOrganicandBiochemistry

Fall2006

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

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Chem212

SurveyofOrganicandBiochemistry

Fall2006

7. (12 pts) For each example, draw two different line angle structures: a. C10H14, with an aromatic ring (may have other functional groups as well) Draw two different structures!

b. C7H14O2, with a carboxylic acid (may have other functional groups as well) Draw two different structures!

c. C5H8O with a ketone (may have other functional groups as well) Draw two different structures!

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Chem212

SurveyofOrganicandBiochemistry

Fall2006

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

.
H2, Pt

HCl

H3C

CH3

Br 2

KMnO 4 H2 O

H2SO 4 H2 O

CH3 Br 2, FeBr 3 CH3 Br 2, Light

H2SO 4, HNO 3

ZnCl 2

H3C HO OH
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OH CH3

Na2Cr2O7 H2SO 4

Chem212

SurveyofOrganicandBiochemistry

Fall2006

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.

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