Chemistry 1152
Review for Exam III
1. Draw correct structures for the following…
a. cyclohexanone
c. 3-methylpentanal
d. diphenyl ketone (benzophenone)
g. methylpropanal
h. 2-butanone
k. ethylphenylketone
2. Write correct names for the following…
O
C
H
b.
c.
C
O
f.
O
H3C CH2 C CH CH2 CH3
CH3
H2C
g. H3C
CH3
O
CH CH CH CH2 CH2 C
H3C
i.
Cl
H3C
CH2 CH2 CH3
C
O
H
k.
H3C
C
O
H3C
5. Define:
a. amylopectin
f. hemiacetyl
m. hydrolysis
b. amylose
j. monosaccharide
n. hyperglycemia
d. aldose
k. acetal
l. glycoside
7. Explain how you would distinguish between a sample of cyclohexanone and
benzaldehyde.
9. Label the following as alpha, beta, or aldose forms of glucose…
H2C OH
O
H
HO
H2C OH
OH
H
H
H
O
H
HO
OH
OH
H2C OH
OH
H
O
H
H
HO
OH
H
O
OH
H
10. What are the differences between amylose, amylopectin, glycogen, cellulose, and
dextrins?
11. React ethanal with an excess of CH3CH2OH.
12. Prepare 2-propanone from an alcohol. Can you prepare propanal from an alcohol?
Can you prepare propanal by some other method?
13. React glucose to make a glucoside.
14.
Is this starch, cellulose, or
something else?
O
O
O
X
H
OH
OH
H
20. Sucrose is sweet. Explain why hot tea will taste sweeter than iced tea when they are
sweetened with equal amounts of sucrose.
21. Is glucose sweet? Is starch? Is cellulose? Is your instructor?
22. Reactions…
Usual rules, if no reaction occurs, write NO REACTION.
a.
O
H3C
+ H2
C
CH2
CH2
Ni
CH3
O
b.
+ H2
H3C C
Pt
H
O
c.
CH
H2C
CH2 C CH3
+ Excess H2
Ni
HO
C
O
R
C H
d.
H
KMnO4
R-CH2OH KMnO4
O
R
R
C H KMnO4
Starch + H2O
O
f.
R'
KMnO4
OH
O
e.
CH
H3C CH2 C
H
H+
Δ
H+
+ CH3OH Δ
CH3CH2OH
H+
O
q.
+ Tollen’s Reagent
C
H
O
r.
H3C
+ CH3OH
C
CH2
H+
H
H+
s. Product of (r) + CH3CH2CH2CH2OH
H2, Pt
O
u)
H3C CH2 C CH CH
H2C OH
x.
β formation
OH
H
HO
OH
H
H
C
O
H
OH
O
z.
H3C CH CH2 CH2 C
CH3
+ Benedict’s Solution
H
α formation
23. More Reactions…
a.
H3C C CH3
H+
+ CH3CH2OH
O
b.
Product of (a) + CH3CH2CH2OH
c.
Product of (b) + H2O
H+
H+
Δ
Pt
d.
O + H2
O
e.
H3C CH CH2 CH2 C
CH3
+ Benedict’s Solution
CH3
k. Glucose + Benedict’s Solution
l. Starch + Benedict’s Solution
m. Cellulose + Benedict’s Solution
n.
H3C
CH2
CH2
CH
CH3
KMnO4
OH
o.
O
KMnO4
p.
O
+ Benedict’s Solution
O CH2 CH3
q.
Dissociation (?)
H3C C H
OH
CH3
r.
O
CH C
H2C
H
CH3
CH3
H3C CH CH2 C
t.
H2, Pt
C
O
KMnO4
H
u.
O
CH3
H3C CH CH2 C CH3 + Tollen’s Reagent
H2C OH
v.
O
H
HO
OH
H
H
H
OH
OH
H+
Δ
w. Product of (v) + H2O
H2C OH
z.
HO
H
H2C OH
O
OH
H
Galactose
H+
+ CH3CH2OH
H
OH
OH
+
H
O
H
HO
OH
H
H
H
β1-4 Connection
OH
OH
Glucose
Lactose
24. Even more reactions…
O CH2 CH3
b. H3C CH
O
g.
Δ
+ H2O
CH2 CH3
OH
O
Intramolecular
H3C CH CH2 CH2 CH2 C
H
29. Draw an aldose hexose that is not glucose.