Exam 4 Sample Problems
Exam 4 Sample Problems
Exam 4 Sample Problems
Dr. Spurgeon
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1. The following names are incorrect (they do not follow the IUPAC rules). Provide a structural formula that fits the incorrect name
and then rename the structure correctly, using the IUPAC rules.
a. (2E)-Hexen-5-one b. 4-Bromo-1-cyclohexen-5-one
2. Show the mechanism for the following formation of a hemiacetal (R2C(OH)OR) – a key functional group in the cyclization of sugars:
O O OH
cat. H A
HO H (acid)
3. Complete the following reaction schemes by providing the necessary product, starting material, and/or reagents in the boxes
provided. Be sure to note any regio- and/or stereocontrol in the reaction. Also, answer any related questions.
Jones
a. Reagent
OH
O
Ag2O
b.
NH4OH
OH H H2O
Br 1. COOH
c. 2.
3.
4. Match the structure with functional group/description
O
O Na Polypeptide
O
Triglyceride (fat/oil)
O
H 2N O O
H H
N N
H 2N N OH
H
O O
Soap
OH
O
Wax
O O
O O
5. Circle the amino acid(s) below that have basic side chain(s).
O O O
H 2N CH C OH H 2N CH C OH H 2N CH C OH
CH3 C O
NH2
HN
O O
O
H 2N CH C OH H 2N CH C OH
H 2N CH C OH
CH2 CH2
CH2
C O CH2
SH
OH CH2
CH2
NH2
6. Pick any three (3) of the amino acids above and draw them as Fischer Projections in their naturally occurring stereochemistry.