Homework Set #7
Chemistry 1315
Spring 2004
___________________________
Name
Handed Out:
Due:
3-26-04
4-1-04 at 9:30am in class
Late Policy:
One day late (4-2-04 10am): 50% off
Two days late (4-3-04 10am): 75% off
After 10am 4-3-04:
no credit
You may work in groups of up to 3 students. However, each student must
make contributions to the answers.
Total:
Questions
Points possible
1
2
3
4
5
6
7
8
10
20
10
10
10
10
20
10
Your Score
100
1
Question #1 (10 points)
Draw beta-L-glucopyranose (cyclic beta-L-glucose) in its most
stable chair conformation. Label the substituents as axial or
equatorial.
2
Question #2 (20 points)
At equilibrium in aqueous solution, D-fructose consists of 70% betapyranose, 2% alpha pyranose, 23% beta furanose, and 5% alpha
furanose forms. Draw all four.
3
Question #3 (10 points)
The two stereoisomers (alpha and beta) of maltose (a disaccharide)
undergo mutarotation which means they interconvert into each
other. Based on your understanding of carbonyl and alcohol
chemistry, provide a mechanism that will account for this exchange.
4
Question #4 (10 points)
D-2-deoxyribose is found in DNA. Draw the structure. Deoxyribose
and ribose form esters with phosphoric acid in DNA and RNA. Can
both monosaccharides react to form the same number of ester
combinations? Show the reactive sites for esterfication.
5
Question #5 (10 points)
Give the IUPAC name for the following carboxylic acids:
A)
H3C
CO2H
CH3
B)
H2C
O
HO
C) H3C
CO2H
6
Question #6 (10 points)
Predict the product from the reaction of phenylacetic acid with each
of the following reagents: a) KOH, b) SOCl2, c) LiAlH4 then H2O,
and d) CH3CH2OH, H+
7
Question #7 (20 points)
Outline a sequence of reaction(s) that will allow pentanal to be
converted into a) pentanoic acid, b) hexanoic acid, and c) 2-hydroxy
hexanoic acid.
8
Question #8 (10 points)
Describe two methods for the preparation of 5-methyl hexanoic acid
from 4-methyl-1-pentanol.
9