Name (This is an open brain exam, those who brought their ...

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)

Org 1 final Page 1

2) Name the classes of compound that the following molecules belong to (E.g. alkane, amide, etc). (13.5pts)

O R O-H

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

O RR

O RH

O R Cl R NH2

Org 1 final Page 2

3) Classify each of the following reactions as either an Elimination, Addition or Substitution. (7.5pts)

(a)

H3C

H

H3C

H

Br

H

(b)

I

H Br

(c) H3C

CH3

Br H

H Br

(d) H3C

CH3

Br H

H3C

CH3

H3C

H

H

CH3

(e) Ph C C:- + CH3-Br

Ph C C CH3

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

CH3CH2OH

CH3CO2 H

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

Org 1 final Page 3

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)

Org 1 final Page 4

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)

Org 1 final Page 5

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