CH 204/214 Exam 2 2024

Java Python CH 204/214

Exam 2

February 29, 2024

I. (24 points)

1. For the following transformations draw the major product in the box below. Draw only one stereoisomer in the box if there is more than one. On the right side check the box(es) that corresponds to the major product obtained from the reaction.

a)

b)

c)

d)

e)

f)

II. (22 points)

g)

h)

i)

2. Molecule 2 was prepared via treatment of molecule 1 with ethyl magnesium bromide followed by a weak acid work-up. Provide a complete curved arrow mechanism for the most straightforward conversion of 1 to 2 using the reagents given.

III. (18 points)

3. Molecule 4 was prepared via treatment of molecule 3 with triphenyl phosphine followed by CH 204/214 Exam 2 2024 a strong base. Provide a complete curved arrow mechanism for the most straightforward conversion of 3 to 4 using the reagents given.

4. When molecule 5 is treated with triphenyl phosphine, followed by a strong base, a compound is produced whose 1 H NMR spectrum is shown here. Draw the product of this reaction in the box below.

5. When aldehyde A and aldehyde B react with water, they form. the corresponding hydrates. Which aldehyde would form. the hydrate faster, circle your answer in the box below (Based on Karty 18.3, 1 point):

IV. (26 points)

6. Propose a sequence of reactions that efficiently converts the given starting material(s) to the target molecule. Draw the structure of the product formed after each synthetic step. Do not write mechanisms. You may only use reactions covered in CH203/218 and CH204/214 (Spring 2023).

a)

b) Indicate the intermediates or reagents in the given boxes below. You do not need to show stereochemistry in the intermediates. Reagents outside of boxes will not be graded