Chem212

SurveyofOrganicandBiochemistry

Summer2006

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Print your full name legibly in the space above.

Exam 1: Ch. 1-5

22 June 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. Draw a reasonable Lewis structure for each of the following, showing all lone pairs and formal charges where relevant: a. H2CO

b. N3- (linear molecule)

c. SO42-

2. State whether the structures in each pair below are the same molecule, cis-trans isomers, constitutional isomers, or not related.
H3C CH3 H3C CH3 CH3 (CH3)3CCH2CH2CH2C(CH3) 2CH2CH2CH3

H3C

CH3 CH3 CH3

H3C

CH3 CH3

H3C CH3

CH3

H3C CH3 CH3

Br

Br CH3

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Chem212

SurveyofOrganicandBiochemistry

Summer2006

3. Answer the following questions about the structure below, which is atorvastatin, or Lipitor , one of the most widely prescribed drugs today.
H3C O e NH 1 f N 2 d 3 F a 4 CH3

OH b

OH

O c OH

a. How many carbon atoms are in the structure? ___________ b. What is the degree of hydrogen deficiency (unsaturation) of the structure? __________ Hint: When using the usual calculation formula, subtract the number of fluorine atoms just like you do with hydrogen. 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. Draw two Newman projections, one for a staggered and one for eclipsed conformations of 2bromo-3-chloropentane looking down the C2-C3 bond:

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Chem212

SurveyofOrganicandBiochemistry

Summer2006

5. Give the chemical name for the following molecules:

CH3 CH3

H3C H3C CH CH3 3

HO

OH

H3C

CH3 O

H3C

OH

H3C

NH2

Br

H3C CH3 CH3

OH

HS

H3C H3C

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Chem212

SurveyofOrganicandBiochemistry

Summer2006

6. 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

Summer2006

7. For each example, draw three different line angle structures: a. C5H10, with an alkene (may have other functional groups as well) Draw three different structures!

b. C8H12O2, with an acid (may have other functional groups as well) Draw three different structures!

c. C6H14O with a tertiary alcohol (may have other functional groups as well) Draw three different structures!

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Chem212

SurveyofOrganicandBiochemistry

Summer2006

8. Draw the structure of the starting materials and the organic products for each of the following reactions. If more than one product can forms, draw only one structure for each. a. 1-Methylcyclopentene treated with hydrogen and a metal catalyst

b. cyclopentane treated with bromine and light

c. 1,4-Dichlorobenzene treated with sulfuric acid (H2SO4) and nitric acid (HNO3)

d. o-chlorophenol treated with sodium hydroxide

e. 1-Pentanol treated with K2Cr2O7

f. trans-2-hexene treated with bromine

g. 1-pentene treated with water and sulfuric acid

h. 2-methyl-2-butanol treated with sulfuric acid and heat

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Chem212

SurveyofOrganicandBiochemistry

Summer2006

9. On each arrow, write the reagents required for each reaction.

OH

H3C

OH

H3C

CH2

H3C OH

CH3

OH CH3 CH3 CH3

10. Draw two molecules of ethanol that have a hydrogen bond between them. Use a dashed line for the hydrogen bond

11. Draw the structure of a compound with the formula C5H10O2 that reacts with bromine and is very soluble in water.

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