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Summer 14 Organic I Final Exam 100pts (graded as 150pts)

Name

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1) (3pts total) Give one definition of a Nucleophile

b) Give one definition of an Electrophile

c) Give one definition of an acid.

2) Briefly explain what is meant the following terms: (8pts total)

Saturated Hydrocarbon

Chiral Molecule

Racemic Mixture

Rate Determining Step

Anti Addition

Thermodynamics

Diastereomer

bond

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3) Name the classes of compound that the following molecules belong to (E.g. alkane,

amide, etc). (5pts)

4) Classify each of the following reactions as an Elimination, Addition or Substitution.

(3pts)

5) (4pts) For ethanol (the starting material in 4b):

How many Hydrogens are there?

How many protic (acidic) Hydrogens ?

What is the hybridization of the Oxygen ?

What would be the approximate bond angle of the C-C-O bond ?

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(6) Write a mechanism (i.e. curly arrows) for this electrophilic addition. (6pts)

(7) Name the following molecules in IUPAC form. (12pts)

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8) Assign R or S to each chiral center in these molecules. (6pts)

9) (i) Write a mechanism (i.e. curly arrows) for this E1 elimination. (6pts)

ii) There is also another (minor) product that is formed from elimination, draw this

product. (1pt)

K+-

OCH3, CH3OH

Br

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10) (i) State two characteristics of an E2 reaction. (2pts)

(ii) State two characteristics of an SN2 reaction. (2pts)

(iii) (2pts) Provide an example of two molecules that are isomers.

11) Give the reagents for the following reactions. (8pts)

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12) Give the products (for a & c), and the reagents (for b & d). (8pts)

13) Write the mechanism for (12a) or (12d). (6pts)

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14) Give the products for the following transformations. (8pts)

15) Write the mechanism for one of the reactions in Q14. (6pts)

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16) (2+2pts) Draw any two different conformations of 1,2-difluoroethane, and indicate

which of the two is of lower energy.

***BONUS POINTS (up to THREE).***

Name up to three different sets of reagents that we encountered this semester that perform

exclusive syn transformations.