Exam 4 Sample Problems

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Campus CHM 231, Exam 4 – Sample Problems

Dr. Spurgeon
__________________________________________________________________________________________

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

Name _____________________________ Name _____________________________

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

CH CH3 CH2 CH2

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.

7. Know your reactions!!

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