Download Chemistry 1152

Chemistry 1152
Review for Exam III—The Sequel — Answers
1. a.
b. CH3 CH2 N CH2 CH3
O
CH2
c. CH3 CH2 CH CH2 C
CH3
H
CH3
NO2
O
d.
O
e.
f.
C
NH
Cl
CH3
g.
CH3
CH
O
h.
O
CH3
C
C
i.
CH2
CH3
HO
NH2
H
O
j.
l.
CH3 CH2
NH
CH3
k.
CH3
C CH2 CH3
CH3
CH3 CH CH
m.
CH CH3
O
C CH2 CH C
NH2
HO
2.
O
NH2
a) diethylamine
b) benzaldehyde
c) diphenyl ketone (benzophenone)
d) ethyldimethylamine
e) ethylmethylpropylammonium chloride
f) 4-methyl-3-hexanone
g) 5-chloro-4-ethyl-6-methylheptanal
h) propylamine
i) 2-pentanone
j) 2-amino-4-bromonitrobenzene
k) propanone (acetone)
l) 4-amino-2-methylbutanal
3. a) secondary
d) tertiary
h) primary
j) primary
l) primary
OH
Chemistry 1152
Review for Exam III—The Sequel
4.
O
C
N CH2 CH3
HN
CH2
CH3
N
CH3
5. a) amylopectin—common form of starch. It is heavily branched with α1-6
connections.
b) amylose—less common form of starch. No α1-6 branches as seen in amylopectin.
c) amylase—enzyme that acts upon starch, hydrolyzing every other glucose which
produces maltose.
d) aldose—aldehyde sugar. This term is often used for the aldehyde form of glucose.
e) inner salt—a form of an amino acid that has allowed its acid and amine groups to
react internally. This produces two ionic dipoles within the molecule.
f) hemiacetyl—functional group formed from aldehyde and alcohol. Four criteria
need to be met: 1) an R—group 2) a Hydrogen 3) an alcohol and 4) an ether all
bonded to the same carbon.
g) enzyme—protein molecule that functions as a biochemical catalyst.
h) protein—large biochemical built from amino acids. This molecule would have
some kind of biological function.
i) peptide—small protein segment, usually 2-50 amino acids in length.
j) monosaccharide—simplest of all carbohydrates. It cannot be broken down further
by hydrolysis.
k) acetal—functional group formed when a hemiacetyl reacts with an alcohol. Four
criteria need to be met: 1) an R—group 2) a Hydrogen 3) an ether 4) another
ether all bonded to the same carbon.
l) glycoside—a carbohydrate acetal formed by reacting a glycose with an alcohol.
m) hydrolysis—reaction with water. Usually applies to the reverse of condensation
reaction.
n) hyperglycemia—a medical condition where the level of glucose in the blood is
above normal.
o) denaturation—the destruction of the tertiary structure of a protein. This often
affects the biological activity of the protein. Note: the primary structure of the
protein remains unchanged.
p) quaternary ammonium salt—an ammonium salt with four R—groups. A picture is
worth a kiloword…
R2
_
+
R1 N R 3 X
R4
Page 2
Chemistry 1152
Review for Exam III—The Sequel
6. CH3CH2CH2CH2NH2
Page 3
butyl amine
primary
2-aminobutane
primary
1-amino-2-methylpropane
primary
methylpropylamine
secondary
isopropylmethylamine
(common name)
secondary
diethylamine
secondary
ethyldimethylamine
tertiary
CH3
CH3
CH2
CH
NH2
CH3
CH3
CH
CH2 NH2
CH3
CH3 CH2 CH2 NH
CH3 CH3
CH3 CH
CH3
CH2
NH
NH
CH2
CH3
CH3
CH3 CH2 N
CH3
Did you find any others?
7. I would use Tollen’s Reagent. A positive test will indicate aldehyde, a negative test
will indicate the ketone.
R1
8.
NH2
R2
R3
CH C
N
CH C
N
O
H
O
H
CH2 OH
9.
OH
H
OH
H
OH
Alpha
C
N
O
H
CH
R5
C
N
O
H
H
OH
OH
H
OH
H
OH
H
CH
C
...
O
CH2 OH
CH2 OH
O
H
CH
R4
OH
Aldose
O
H
H
OH
C
O
OH
H
H
OH
OH
H
Beta
10. Amylose, amylopectin, glycogen and dextrins are all starches. Amylose is the
straight chain type, amylopectin is branched, glycogen is heavily branched and is
the human form of starch. Dextrins are branched oligosaccharides formed from
the partial hydrolysis of amylopectin. Cellulose is the β1-4 glucose polymer that
cannot be digested by humans.
Chemistry 1152
Review for Exam III—The Sequel
Page 4
OH
O
OH
OH
11. CH C
3
CH3 CH2
+
CH3
CH3
O CH2 CH3
CH3 CH2
C O CH2
H
CH3
C
H
H
hemiacetal
OH
12.
O CH2 CH3
acetal
O
KMnO4
CH3
CH3 CH CH3
C
CH3
One cannot make propanal from an alcohol as the primary alcohol would further
oxidize to a carboxylic acid. It can however, be made, but not by a reaction we
are familiar with.
CH2 OH
13.
CH2 OH
O
H
OH
+
H
H
CH3 OH
OH
OH
O
H
H
H
OH
H
H
OH
O
OH
OH
CH3
glucoside = glycoside of glucose
14. This is the β1-4 polymer of glucose, which is cellulose.
CH3
15.
CH3 CH
O
CH
CH3 CH
+
Acidic
CH3
C
CH3
16.
CH3
N
+
CH
C
+
OH
NH3
O
CH3
_
CH3 CH
O
Neutral NH3
C
Basic NH2
CH3
_
O
C CH2 CH2 CH3
_
O
CH3
CH3
17.
NH2
CH
O
CH3
H
O
CH3
CH3
CH
CH C
N
CH C
N
O
H
O
H
CH
CH3
CH
H
C
N
O
H
CH
OH
CH2
C
N
O
H
CH
H
CH2
C N CH C N CH C
O H
O H
OH
O
18. Denaturing affects the tertiary bonding (salt bridges, hydrogen bonding, disulfide
bonds).
19.
O
O
O
O
O
O
...
H2N (CH2)6 NH C (CH2)4 C NH (CH2)6 NH C (CH2)4 C NH (CH2)6 NH C (CH2)4 C
Chemistry 1152
Review for Exam III—The Sequel
Page 5
20. Hot tea will hydrolyze the sucrose into glucose and fructose. The sum of sweetness
from glucose and fructose is greater than the sweetness from sucrose alone.
21. Glucose is sweet, it is a monosaccharide. Starch is not sweet, neither is cellulose as
the polymers are too large. Of course, the instructor is sweet, very sweet.
22.
a. CH
3
O
CH2
CH2
OH
C CH3 + H2
O
b. CH3 C
Pt
+ H2
Ni
CH3 CH2
CH2
CH CH3
CH3 CH2 OH
H
O
c. CH2 CH
OH
CH3 CH2
CH2 C CH3
CH2 CH CH3
Ni
+ Excess H2
OH
OH
C
O
CH2 OH
H
d.
R
C
R
KMnO4
No Reaction
R CH2
OH KMnO
4
R
O
R
OH
O
C
H KMnO
4
R
O
e.
C
C
OH
R
O
Starch + H2O
H+
+
ΔH
Δ
Glucose
O
H+

f. CH3 CH2 C + CH3 OH
H
O
g. CH3 C
+ H2
H
R
KMnO4
OH
OH
H+
Δ
CH3 CH2 OH
CH3 CH2 C O CH3
CH3 CH2 OH
R
C
R
O
Protein + H2O
H
Pt
CH
Amino Acids
O CH2 CH3
CH3 CH2 C O CH3
H
Chemistry 1152
Review for Exam III—The Sequel
Page 6
CH3
CH3
h.
N CH2 CH3
_
+
+ HBr
Br
N CH2 CH3
H
CH3
i.
CH3
N
+ CH3 CH2 Cl
CH3
CH3
_
Cl
H2C CH3
NaOH
j. ethylmethylamine + 1-chloropropane
O
k. R C
CH3
+
N CH3
ethylmethylpropylamine
O
+ CH3 NH2
R C
Cl
HN CH3
O
CH3 CH2 CH2 C
l.
O
CH3 CH2 CH2 C
CH2 CH3
OH
_
CH2 CH3
O
CH3 NH
+
+
CH3 NH 2
O

+ H2O
CH3 CH2 CH2 C
N CH3
CH2 CH3
O
m.
O
C
+ NH3
Cl
NH2
O
n. CH3 CH2 CH2 C
H+

+ H2O
NH CH3
NaOH
o. NH3 + CH3Cl
CH3
N
O
+
CH3
+
CH3 CH2 CH2 C
NH2 CH3 + NaCl + H2O
O
CH3
CH3 CH2 C
CH3
OH
N
+
CH3
+
CH3 CH2 C
H
O
+ Tollen’s Reagent
C
C
H
Positive Reaction
OH
O
r.
_
O
O
q.
NH2 CH3
OH
O
CH3
p.
+ HCl
C
CH3 CH2 C + CH3 OH
H
H+
CH3
OH
CH2
C O CH3
H
Chemistry 1152
Review for Exam III—The Sequel
s. Product of (r) + CH3CH2CH2CH2OH
Partial
hydrolysis
t) amylopectin
H+
Page 7
CH3
O CH2 CH2 CH2 CH3
CH2
C O CH3
H
Complete
hydrolysis
Dextrins (Oligosaccharides)
glucose (monosaccharides)
OH
H2
CH3 CH2 CH CH2 CH2
Pt
O
u)
CH3 CH2 C CH CH
OH
NaBH4
CH3 CH2 CH CH CH
v)
O
NH
O
+ CH3 CH2 CH2 C
CH2 CH3
CH3 CH2 CH2
OH
C
+ NH
_
O
2
CH3 CH2
CH3
O
+
CH3
CH3 NH 2 + CH3 CH2 CH2 C _
O
O
w. CH NH + CH3 CH2 CH2 C
3
OH
O

+
CH3 CH2 CH2 C
HOH
N CH3
CH3
CH2 OH
CH2 OH
O
H
x.
OH
H
OH
H
OH -formation
H
H
OH
OH
H
OH
y. . CH3CH=CHCH3 + O2

CH2 OH
OH
O
H
OH
CO2 + H2O
C
H
O
-formation H
OH
H
H
OH
OH
H
OH
Chemistry 1152
Review for Exam III—The Sequel
Page 8
O
Positive Results
+ Benedict's Solution
z. CH3 CH CH2 CH2 C
H
CH3
CH3
23.
a. CH3 C
CH3
H+
CH3 CH2 OH
+
CH3
C O CH2 CH3
O
OH
CH3
H+
b. Product of (a) + CH3CH2CH2OH
CH3
C O CH2 CH3
O CH2 CH2 CH3
CH3
H+
c. Product of (b) + H2O
CH3

C O CH2 CH3
+
CH3 CH2 CH2
OH
Pt
d.
OH
O + H2
O
e. CH3 CH CH2 CH2 C
Negative Results
+ Benedict's Solution
CH3
CH3
O

O
f.
+ H2O
CH3 C
NH2
+ NH3
CH3 C
O
OH
CH3 C
O
g.
CH3
C
N
O
CH3
CH3
+ H2O
_
O

+
CH3 C
OH
NaOH
h. CH3CH2NH2 + CH3Cl
NH CH2 CH3
i.
CH3
NH2-CH3
CH3NH3+ Cl¯ + NaOH
j. Cellulose + O2
Δ
NH4+
CO2 + H2O
NH CH3
CH3
OH
Chemistry 1152
Review for Exam III—The Sequel
k. Glucose + Benedict’s Solution
Positive Test
l. Starch + Benedict’s Solution
Negative Test
m. Cellulose + Benedict’s Solution
Negative Test
n.
CH3 CH2 CH CH2 CH3
KMnO4
CH3 CH2 C
OH
o.
KMnO4
No Reaction
+ Benedict’s Solution
O
Negative Test
O CH2 CH3
q.
CH2 CH3
O
O
p.
Page 9
O
dissociation (?)
CH3 C H
+
CH3 C
CH3 CH2 OH
H
OH
CH3
LiAlH4
CH2
CH C
CH3 O
r.
CH2
CH C
CH2 OH
CH3
C
H
CH3
H2, Pt
CH3
CH3
CH2 C
CH2 OH
CH3
s.
NH2 + HCl
CH3
t.
O
CH3 CH CH2 C H + Tollen's Reagent
_
+
NH3 Cl
CH3
O
CH3 CH CH2 C OH
Positive Result
CH3
u.
O
CH3 CH CH2 C CH3 + Tollen's Reagent
Negative Result
Chemistry 1152
Review for Exam III—The Sequel
CH2 OH
CH2 OH
O
H
v.
OH
H
O
H
H+
+ CH3CH2OH
H
OH
OH
H
Page 10
OH
H
H
OH
H+
w. Product of (v) + H2O
The reactants of (v)
Δ
CH3
CH3
x. CH3 CH2 N
+
NaOH
CH3 CH2 Cl
+
CH3 CH2 N CH2 CH3
CH2 CH3
CH2 CH3
O
O
H+

+ H2O
C
CH2OH
OH
CH2OH
O
HO
OH
OH H
H
H
H
H
CH2OH
O
+
OH
H
OH
OH
+ NH3
C
NH2
z.
O CH2 CH3
OH
OH
y.
H
H
Galactose
H
1-4 Connection
OH
CH2OH
O
HO
OH
H
H
OH
O
H
H
OH
O
H
Glucose
OH
H
H
OH
H
OH
Lactose
24. Even more reactions…
O
a. CH3 CH2 NH
+
CH3 CH2 C
CH2 CH3
O

+ H2O
CH3 CH2 C
N CH2 CH3
OH
CH2 CH3
O CH2
b.
CH3
CH
+ H2O
O CH2
c.
CH3

O CH2
CH3
CH3
NH2
+
An enzyme + H2O
HO CH2 CH3

O
+ H2O
C
HN
OH
d.
+
OH
O
C
CH
CH3
H+
Δ
amino acids
Chemistry 1152
Review for Exam III—The Sequel
Enzymes
Synthesis
e. Amino acids
protein
O
f.
O
+
CH3 CH2 C
Page 11
CH3
NH2
+ HCl
CH3 CH2 C
Cl
NH CH3
CH3
O
OH
O
Intramolecular
g. CH CH CH CH CH C
3
2
2
2
H
OH
H
25. Heat can be used as a denaturing agent. The elevated heat denatures the protein
enzyme and it stops working.
O
26.
R CH
NH2
C
OH
27. The primary structure is the order or sequence of amino acids that make up the
protein chain. The secondary structure occurs due to natural bonding angles of
the atoms in the chain and the tertiary structure is the 3-dimensional shape or
folding that the chain does to create a 3-dimensional “sculpture” of the protein. It
is often this 3-dimensional character that gives the protein its function ability.
28. The amine compounds are rather insoluble. By acidifying and making the amine into
a salt one creates an ionic bond and solubility is greatly increased.
CH2 OH
29.
O
HO
OH
H
H
OH
or
OH
HO
H
OH
H
H
OH
H
H
Notice that the -OH
group is in a different
orientation here than
it is in glucose.
CH2 OH
OH
O
C
H
Galactose in the aldose form
30. Biochemistry Reactions. Complete…
A. Starch + H2O
H+

polymerization
oligosaccharides
Partial hydrolysis
glucose
Complete hydrolysis
Chemistry 1152
Review for Exam III—The Sequel
B. Monosaccharide
Page 12
polysaccharide
C. Cellulose + H2O
H+
oligosaccharides

glucose
Partial hydrolysis
Complete hydrolysis
+
H
D. Proteins + H2O
peptides

amino acids
Complete hydrolysis
Partial hydrolysis
E. Starch + Benedict’s Solution
negative test
31.
CH2 OH
CH2 OH
O
H
OH
H
O
H
H
OH
CH2 OH
OH
H
H
OH
O
H
OH
H
O
H
OH
H
H
OH
OH
B.
H
O
A.
A.
C. The polysaccharide would be starch.
32. Our bodies have the enzymes necessary to digest the 1-4 bonds but we lack the
enzymes necessary to digest the 1-4 bonds. Termites and cud chewing animals have
microorganisms in their digestive tracts that can digest the 1-4 bonds.
33. Butanal would be made by oxidation of an alcohol, but our method converts a
primary alcohol all the way to an acid so it does not stop at the aldehyde.