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

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(1 a-j) are TRUE/FALSE (10pts)

a) A nucleophile is a two electron donor.

b) One definition of an acid is a proton donor.

c) All alkynes have a carbon-carbon triple bond.

d) A Lewis base is a two electron donor.

e) A chiral molecule has an identical mirror image.

f) The rate determining step is always the quickest step.

g) An anion has a positive charge.

h) Acyclic compounds can have ring strain.

i) Saturated compounds have the maximum number of bonds to hydrogen.

j) Kinetics deals with the speed of chemical reactions.

2) Define the following terms (4pts): Addition reaction

Elimination reaction

Racemic mixture

Structural isomer

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3) Name the classes of compound that the following molecules belong to (E.g. alkane, amide, etc). (6pts)

4) (3pts) For cyclopentane:

How many Carbons are there ?

How many Hydrogens ? What is the hybridization of the Carbons ?

5) Write a mechanism (i.e. curly arrows) for this electrophilic addition. (5pts)

What name is given to the regiochemistry of this reaction ? (1pt)

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

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

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

9) a) Draw using line angle diagrams (stick figures) three different isomers of butene. (3pts) b) Indicate which of the three is most stable. (1pt) c) Draw using line angle diagrams (stick figures) two different isomers of ethylcyclohexane (2pts) d) Indicate which of the two is more stable (1pt).

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10) Give the reagents for the following alkene reactions. (8pts)

11) Give the reagents (for a, b & d), and the products (for c & e). (10pts)

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12) Draw in the arrows for the following anti addition mechanism. (5pts)

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

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14) Draw in the arrows for the following mechanism. (5pts)

15) (3+1pts) Draw any two different conformations of 1,2-difluoroethane in Newman

projection form, and indicate which of the two is of lower energy.

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

-What is the name of –[OCN] anion ? -Why is the SH group called a mercapto- substituent ? -List reagents to accomplish the below (multistep) transformation.

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