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Final Exam for Organic I

200pts (graded as 300pts)

Name
(This is an "open brain" exam, those who brought their brain, are
encouraged to keep it open during the examination).
1) Explain in a simple sentence what is meant in a chemical sense by the
following arrows. (7.5 pts)
(a)

(b)

(c)

(d)

(e)

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2) Name the classes of compound that the following molecules belong to


(E.g. alkane, amide, etc). (13.5pts)
O
R

O-H
O

O-R

R-C C-R
R O-H
R O-R
O
R

R
O

H
O

Cl

R NH2

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3) Classify each of the following reactions as either an Elimination,


Addition or Substitution. (7.5pts)

(a)

H3C

(b)

(c)

H3C

Br

H
H

H Br
H3C

H3C

CH3

CH3

Br H

(d)

H Br
H3C

H3C

CH3

Br H

(e) Ph C C:-

H
CH3

Ph C C CH3

+ CH3-Br

4) Draw Lewis structures (sticks for bonds, and dots for lone pairs) for the
below two molecules. (6.5pts)
CH3CH2OH

CH3CO2H

5) For the above two molecules, label the hybridization of all the carbons
and oxygens. (5pts)

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6) Explain why ethanoic acid is a much stronger acid than ethanol. (10pts)

7) On the below energy level diagram, label (a) the axes (b) the reactants
and products (c) any transitions states (d) Ho for the overall reaction (e)
is this reaction exothermic or endothermic (f) is this reaction more likely
to proceed by an E1 or E2 mechanism? (10pts)

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8) Explain why CH3+ (methyl cation) has a different three dimensional


geometry to CH3- (methyl anion). (12pts)

9) Briefly explain which of the two above geometries best describes CH3
(methyl radical)? (3pts)

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10)

Name the following molecules in IUPAC form. (16pts)


(a)

(b)

(c)

(d)
F
OH
(e)

Br

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11) Asterix any chiral atoms in these molecules, and assign R or S to each
chiral center. (15pts)
H

(a)

(b)

Cl
F

CH3

F
F
F
F

F
F
F
F

CH3
CF3

(c)

(d)

H
H

CH2F
Cl
Cl
CH2F

12) Which of the above molecules are achiral, and in a sentence explain
why they are achiral. (4pts)

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13) Circle the more stable member of each pair, and in a sentence explain
your choice. (15pts)
+
(a)

(b)

CH2

(c)

CH2

(d)

+
CH2

(e)

14) Name two of the geometrical conformations a cyclohexane molecule


can adopt. (2pts)

15) Name the two different positions that the hydrogens of cyclohexane
can be located in the more stable geometrical conformation. (2pts)

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16) Even in its most stable geometry, Bromo-cyclohexane can exist as


two conformers. Draw these two conformers, and label which is the more
stable, and in a sentence explain why one is more stable. (10pts)

17) Name the two allowed geometries for any elimination reaction to
proceed. (3pts)

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18) Which conformation of bromocyclohexane in (16) undergoes reaction


with potassium tbutoxide, and explain in a sentence your choice. (4pts)

19) Provide a mechanistic explanation for the observed mixture of


products in the following SN1 reaction. (10pts)
D2C

H
C

CH3OH
CH2-Br

SN1

D2C

H
C

C
H2

OCH3

H2C

H
C

C
D2

OCH3

20) What would you expect the approximate ratio of these products to be?
(2pts)

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21)

Give the products of 5 of the 6 following reactions. (15pts)

(a)

H3C

(d)

(e)

(f)

2) CH3CH2Br

1) Mg, Ether

(b)

(c)

1) NaNH2

H3C

2) D2O

HBr, Peroxides

CH3

1) BH3.THF

CH3

2) H2O2, NaOH

CH3

1) Hg(OAc)2,H2O

CH3

2) NaBH4

H3C

1) Na, NH3

21b) Write the mechanism for one of the above anti-Markovnikov additions.
(6pts)

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22)

Give reagents to perform 5 of the 6 following transformations. (15pts)

(a)

OH

O
(b)

(c)

O
O C CH3

OH O
O

H3C

(d)

NH2

OH

H OH

(e)

Cl H
Br
(f)

H3C

H
Br

22b) Write the mechanism for either of the above alkyne reactions. (6pts)

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