University of California San Diego Organic Chemistry Worksheet I have this organic chemistry worksheet, only 4 questions. I attached the worksheet below! S

University of California San Diego Organic Chemistry Worksheet I have this organic chemistry worksheet, only 4 questions. I attached the worksheet below! Solve on a separate sheet of paper and scan it. Thank you Quiz, 7/20/20
Name:
Question 1: For each pair of compounds below, circle the compound that is the best electrophile.
O
O
O
N
a.)
O
O
O
O
O
b.)
Cl
O
H
O
O
c.)
Question 2: A.) Suggest an acyl chloride and an amine that could be used to form the product below. B.) Ordinarily,
two equivalents of an amine are required to efficiently form an amide from an acyl chloride. What is the purpose of the
second molecule of amine? (Hint: Try to write out the mechanism without using a solvent on a separate piece of
paper.) C.) Given that the pKa of HF is around 3.2 and the pKa of HCl is around -7, would you expect the product to be
formed faster or slower if an acyl fluoride were used instead of an acyl chloride?
O
N
H
a.)
b.)
c.)
3.) Synthesis (CHOOSE ONE): Provide a reasonable sequence of reactions to complete the following transformation.
O
OH
O
i.)
O
OH
O
O
ii.)
O
4.) Mechanisms (CHOOSE ONE): Use proper arrow formalism to diagram one of the following transformations:
CH3O- Na+
O
i.)
O
O
O
ii.)
CH3OH
O
O
(plus a second major organic product…what is it?)
1.) LiAlH4 (excess), ether
O
2.) H3O+ workup
OH

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