Download Fall, 2002

CHEMISTRY 1152
EXAM III
Fall, 2002
NAME__________________________
All notes, books, etc., must be placed out of sight. Please read each of the problems
carefully. If something is not clear, please ask.
The exam consists of 11 problems on 4 pages with some extra credit on the fifth page. Make
sure your exam is complete. The exam is worth 100 points with each of the problems labeled
as to its point value.
Answers should be placed in the space provided. Write legibly--if I cannot read it--it is
wrong. Please include an explanation whenever asked to or whenever necessary to make
your answer clear. Please put your name on every page of the exam.
As usual, no cheating is allowed. Good Luck!!!
Chemistry 1152
1
Name________________________
1.(12) Name each of these structures correctly using systematic names…
A.
B.
O
O
C
CH2
H3C
CH2
H3C
C.
N
CH3
CH3
D.
+
H3N
CH3
_
Cl
2.(12) Draw correct structures for each of the following…
A. 4-methylpentanal
B. 2-bromo-4-methylbenzaldehyde
C. amino acid in acidic solution
D. 2-aminobutane
3.(3) The amide C5H11NO yields ethylamine on hydrolysis. Identify the other product.
4.(36) Complete the following reactions. If no reaction occurs, write NO REACTION.
O
H3C CH2 CH2 C
H
Chemistry 1152
A.
2
Name________________________
H+
CH3OH +
B. The “Product” of “A” + CH3CH2CH2CH2CH2OH
O
+
C. H C NH
3
3
Δ
+ H3C CH2 CH2 C
O
O
D.
_
KMnO4
H3C CH2 CH2 C
H
KMnO4
E.
O

O
F.
H3C
C
NH CH3
+ H2O
OH
CH CH3
G.
NaOH
H. CH3NH2 + CH3CH2CH2Cl
O
I.&J.
Δ
+ CH3NH2
H3C C
OH
O
J.&K. H3C CH CH CH2 C
H
LiAlH4
H2
Pt
You supply correct reactants
and conditions
Chemistry 1152
3
Name________________________
5.(4) Cocaine that is snorted or injected is really the hydrochloride salt of cocaine which is
readily soluble in mucous membranes or blood. This salt is shown here. Crack cocaine
or crack is free base cocaine, the neutral amine, usually made by neutralizing the amine
salt with NaOH. Create crack here by that reaction:
CH3
+ NH
O
C
O
H
CH3
NaOH
O
O
C
H
6.(5)
H3C
N
CH3
+ R-Cl
CH3
If the R group is a long alkyl group, of what use is this product?
7.(5) A lactam is a cyclic amide and can be formed by two functional groups reacting with
themselves in the same molecule (much like glucose does). Do that reaction here for 5aminopentanoic acid.
O
H2C CH2 CH2 CH2 C
NH2
OH
Δ
Chemistry 1152
4
8.(4) Draw the structure of:
Name________________________
(NH2)-Cys·Asn·Met·Leu-(COOH)
9.(4) An unknown is either an amine or an amide. What simple chemical test can you
perform to distinguish between these two possibilities?
10.(5) The structure of raffinose, a trisaccharide found in
some plants, is shown here. If this molecule has an acetal
linkage, draw an arrow that points to it. If it has a
hemiacetal carbon, circle it. Would you expect this to be a
reducing sugar?
HO
OH
O
H
OH
O
OH
O
H
OH
OH
OH
O
HO
O
HO
OH
OH
11.(10) Complete each of the following…
A. Polysaccharide + H2O
H+
Δ
B. Polysaccharide + Tollen’s Reagent
C. Amino Acids
D. Proteins + H2O
E. Amylopectin
Synthesis
Enzymes
partial
hydrolysis
complete
hydrolysis
Chemistry 1152
5
Name________________________
Extra Credit #1. Formaldehyde (methanal) is useful for preserving biological specimens and
embalming cadavers. It kills microorganisms by inactivating their proteins by reacting with
their amine groups (-NH2). The reaction is a dehydration between the amine and the
carbonyl group with the formationof a C=N double bond. Write the equation for this reaction
with this simple amine, CH3-NH2.
Extra Credit #2. Consider…
A mosquito was heard to complain
That a chemist had poisoned his brain
The cause of his sorrow
You should know by tomorrow
Was para-dichlorodiphenyltrichloroethane.
Write me an original poem
about Chemistry for some extra points.