Organic Chemistry

(Dana P.) #1
Problems 333

c. d.


  1. How could one use UV spectroscopy to distinguish between the compounds in each of the following pairs?


a.

b.

c.

d.


  1. What two sets of a conjugated diene and a dienophile could be used to prepare the following compound?

  2. a. Which dienophile is more reactive in a Diels–Alder reaction?


b. Which diene is more reactive in a Diels–Alder reaction?


  1. Cyclopentadiene can react with itself in a Diels–Alder reaction. Draw the endo and exo products.

  2. Which diene and which dienophile could be used to prepare each of the following compounds?


a. c.

b. d.

O

O

O

Cl

Cl

CN

CN

C
O CH 3

CH 2 CHCH CHOCH 3 or CH 2 CHCH CHCH 2 OCH 3

O


  1. CH 2 CHCH or 2.


O

CH 2 CHCH 2 CH

O

CH 2 CHCH or CH 2 CHCH 3

O

CCH 3

and

OH OCH 3

O

and

O

CH 2 CHCH CHCH CH 2 and CH 2 CHCH CHCCH 3

O

and

CH 2 CH C CH 2 + CH 2 CHCH 2 Cl


CH 2 CH C CH 2 + CH 2 CHCCH 3 ∆

O
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