Sp2011 Org II Exam #1 Ch 14-17 (100 points)

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1-15) are True or False (15pts)

1) Benzene undergoes electrophilic aromatic substitution (EAS)

reactions with reactive electrophiles.

2) The EAS reaction mechanism involves an initial loss of aromaticity.

3) Para substitution means a 1,3 arrangement on a benzene ring.

4) The rate determining step in an EAS is the formation of a resonance

stabilized radical.

5) Anti-aromatic compounds have a closed bonding shell of π electrons.

6) For EAS reactions, all deactivators are meta directors.

7) Dioxanes are seven membered heterocycles.

8) Chlorine is a meta directing, activating substituent for EAS reactions.

9) Anti-aromatic compounds are more stable than non-aromatic

compounds.

10) Cyclopentane has less ring strain than an epoxide.

11) Cyclobutadiene is more stable than butadiene.

12)
The oxygen atom in this epoxide
O
is sp3 hybridized

13) Epoxides are more reactive than normal ethers.

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14) Kinetic products are always formed faster than thermodynamic products.

15)
is a bonding
Molecular Orbital

16) Indicate which of the following molecules are aromatic, non-aromatic or

anti-aromatic. (Assume all the molecules are planar). (16pts)

H H
N S
+

CH3
Al

CH3
O
+

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17) Predict the products in the following reactions, paying attention to
regio/stereochemistry where applicable. (24pts)

Excess HI
O

1) NaOH
OH
2) CH3I

CH3

CO, HCl
CuCl, AlCl3

O heat
H H

H3C CH3

SO3, H2SO4
Br

NO2

Cl2, AlCl3

CF3 heat

CH3
Br2, FeBr3

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18) Explain briefly why each of the following attempted reactions are
fundamentally flawed, and will not work. (10pts)

Friedal Craft
Acylation
NO2 NO REACTION

CF3 Diels-Alder
NO REACTION
CF3

2+2 Thermal
Cycloaddition
NO REACTION

Nucleophilic Aromatic
Substitution
NO REACTION

Cl2
NO REACTION

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19) Some chemical species are not accurately described by a single Lewis
Structure. Draw a Lewis structure of an example of such a….. (8pts)

a) Neutral Compound b) Carbanion

c) Carbocation d) Radical

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20) The following compound was produced in a Diels-Alder reaction.
(2+2+2+3+3 = 12pts)
CO2H
CO2H

a) How many sp3 hybridized carbons are in this molecule ?

b) Is this molecule chiral ?

c) Are the carboxylic acid substituents electron donating or electron

withdrawing?

d) Briefly explain your answer to (c).

e) Draw the diene and dienophile which would react together to give
this product.

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21) Give reagents for the following multistep transformations.
(4+3+3+5 = 15pts)

CH2CH3 CH2CH3

OH
OH
in a 1:1 ratio

CH2CH3 CO2H
Cl

Br
NO2

Br

NO2

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BONUS Points (up to 3 points)

Explain why Benzyne is correctly described as a 6π aromatic molecule when

in fact it has a total of 8π electrons.

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