SCC Aldehydes Ketones Carboxylic Acids Esters Amines and Amides Questions Includes multiple choices, true/false, naming IUPAC, reactions, and short answers

SCC Aldehydes Ketones Carboxylic Acids Esters Amines and Amides Questions Includes multiple choices, true/false, naming IUPAC, reactions, and short answers Part I. Multiple Choice
1. What structural characteristic is shared by the aldehydes and the ketones?
a.
b.
c.
d.
They both are straight chain compounds.
Both of these compound classes have as the smallest compound a 5 carbon skeleton.
Aldehydes and ketones both contain a carbonyl carbon.
Aldehydes and ketones have no shared characteristics.
2. The name 4,5-dichlorocyclohexanone should be
a. 1,2-dichlorocyclohexanone.
b. 2,3-dichlorocyclohexanone.
c. 3,4-dichlorocyclohexanone.
d. 4,5-dichlorocyclohexanone.
3. Which of the following pure compounds can exhibit hydrogen bonding with itself?
4. What is the major difference between a cyclic hemiacetal and a cyclic acetal?
a. The cyclic hemiacetal is an alcohol, whereas the cyclic acetal is an ether.
b. The cyclic hemiacetal is an acid, and the cyclic acetal is a base.
c. The cyclic hemiacetal contains more carbons in the ring than the cyclic acetal.
d. All of the responses are correct.
5. Which of the following properly ranks the relative aqueous solubility of each functional group?
a. alkene aldehyde > ketone > carboxylic acid
b. alkene > alcohol > aldehyde > carboxylic acid
c. ketone > alcohol > carboxylic acid > aldehyde
d. alcohol > alkene > ketone > aldehyde
11. The following amine is a ____ amine.
a.
b.
c.
d.
Primary
Secondary
Tertiary
Quaternary
12. Which of the following is the best representation for hydrogen bonding in methylamine, as
indicated by a dashed line?
13. What is a characteristic of amines that is attributed to molecular size?
a. The larger amines have an odor like that of decaying fish.
b. The larger amines have a boiling point near room temperature.
c. The solid amines always have a branched chain structure.
d. Strong hydrogen bonding of the tertiary amines explains their boiling points.
14. Which of the following four-carbon amides would be the least soluble in water?
a. simple amides
b. monosubstituted amides
c. disubstituted amides
d. all would be equally soluble
15. Some amine drugs are administered in the form of salts in order to
a. make them form into pills more easily.
b. make them taste better.
c. make them more basic.
d. make them more soluble in body fluids.
Part II. True or False
1. Only alcohols contain an oxygen bearing functional group.
________
2. Aldehydes & alcohols hydrogen bond with H2O; whereas ketones cannot.
________
3. The simplest ketone has three carbon atoms.
________
4. The carboxyl group found in carboxylic acids must be on a terminal carbon.
________
5. Pure liquid carboxylic acids are strongly hydrogen bonded
even in the absence of water.
________
6. A quaternary amine, like choline, has an overall charge and
can form a salt with something like chloride
________
7. The predominant form of 1-propanamine at low pH values is CH3–CH2–CH2–NH3+ ________
8. Based on the IUPAC name, N,N-dimethylaniline is a secondary amine.
________
9. The amine salts tend to be less soluble than the amine.
________
10. Aniline is the starting block for many of the aromatic amines.
________
Part III. Naming.
1. (9 pts) Fill in table with the missing information. Each molecule in each row should have a
skeletal formula, an IUPAC name, and a functional class identified.
A.
Skeletal Formula:
Functional Class present:
IUPAC Name:
B.
Skeletal Formula:
Functional Class present:
IUPAC Name: Sodium 2-ethyl-3-methylbenzoate
C.
Skeletal Formula:
Functional Class present:
IUPAC Name:
D.
Skeletal Formula:
Functional Class present:
IUPAC Name: N-ethyl-N-methyloctanamide
E.
Skeletal Formula:
Functional Class present:
IUPAC Name: tert-butyl-4-bromohexanoate
F.
Skeletal Formula:
Functional Class present:
IUPAC Name: 2,3-difluorobutanal
G.
Skeletal Formula:
Functional Class present:
IUPAC Name:
Part IV Reactions (30 pts)
Fill in the missing information for each chemical reaction by adding the skeletal structures and
IUPAC names for the reactants and/or products missing (indicated by a “?” for a missing skeletal
structure or ____ for a missing name) needed to complete the reaction. Additionally, name the type
of reaction when asked for.
A.
(O)
?
Names:
_________________
_______________________
Type of reaction:
(O)
B.
(O)
?
?
?
Names:
1-butanol
________________
_________________
Type of reaction:
C.
+ H2 O
+
?
?
Names:
_________________
________
_______________
___________
Type of reaction:
D.
+
+
?
?
?
Names:
____________________
(bonus point)
methanamine
E.
Heat
H2SO4
_______________
____________
+ H2 O
+
?
?
_________________
______________
Names:
_________________
_________
Type of reaction:
F.
+
?
?
?
Names:
_________________
potassium hydroxide
_______________
_________
Type of reaction:
G.
Heat
HCl
+
+
?
?
?
Names:
_________________
Type of reaction:
water
_______________
ammonium chloride
Part V. Short answer (24 pts)
This is the molecule commonly known as Doxorubicin. Doxorubicin is used in chemotherapy to
inhibit uncontrolled cell growth, a hallmark of cancerous cells. Doxorubicin specifically inhibits an
enzyme called topoisomerase which helps remove supercoils in DNA as DNA is replicated during
cell growth and division (mitosis).
Indicate the functional groups a part of Doxorubicin using the following key to label the different
parts of the molecule (note not all functional groups listed may be a part of Doxorubicin):
Alcohol label with an A
Aldehyde label with an H
Ester label with an R
Phenol label with a P
Carboxylic Acid label with a C
Ketone label with a K
Amine label with an M
Aromatic label with a B
Ketal label with a T
Acetal label with an L
Amide label with a D
Ether label with an E
R
|
*
+ H2 O
Here is an abbreviated view of Doxorubicin with a large portion of the molecule
abbreviated with the “R” carbon chain. With your knowledge of Chem 131, you recognize
the asterisked carbon on the lower portion of Doxorubicin as a part of a functional group
you are familiar with and how it is synthesized. Create a reaction scheme starting with the
single molecule containing an aldehyde and alcohol. Show the structure of the intermediate
formed and the subsequent reaction with the additional alcohol to create the final product
shown above (use the R abbreviation to indicate the rest of Doxorubicin when needed).
Doxorubicin is able to inhibit the enzyme topoisomerase and DNA replication by
disrupting the intermolecular bonds that hold the 2 strands of DNA together (a process
called “intercalation”). What 3 potential types of intermolecular forces could Doxorubicin
create with the strands of DNA and give an example of a functional group present on
Doxorubicin that could create that intermolecular bond?

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