CHEM 30B: Midterm Exam 1
Name:_____________________________________________
(100 points)
1.
How many hydrogen atoms are present at the carbon indicated below?
a. 0
b. 1
c. 2
d. 3
e. 4
2.
What is the molecular formula of the molecule below?
a. C9H16O
b. C8H14O
c. C6H12O
d. C5H12O
e. None of the above.
3.
What is the molecular formula of the molecule below?
a. C6H6O2
b. C6H4O2
c. C7H4O2
d. C7H6O2
e. None of the above.
4.
Considering all of the atoms coming off the atom, what is the shape of the carbon indicated below?
a. Bent
b. Square planar
c. Trigonal pyramidal
d. Trigonal planar
e. Tetrahedral
5.
What is the C—C—C bond angle below?
a. 180o
b. 120o
c. 109.5o
d. 90o
e. 60o
6.
What is the relationship between the two molecules below?
a.
b.
c.
d.
Constitutional Isomers
Stereoisomers
Different conformations of the same molecule
Different molecules altogether (NOT isomers)
7.
What is the relationship between the two molecules below?
a.
b.
c.
d.
Constitutional Isomers
Stereoisomers
Different conformations of the same molecule
Different molecules altogether (NOT isomers)
8.
What is the relationship between the two molecules below?
a. Constitutional Isomers
b. Stereoisomers
c. Different conformation of the same molecule
d. Different molecules altogether (NOT isomers)
9.
What is the relationship between the two molecules below?
a.
b.
c.
d.
Constitutional Isomers
Stereoisomers
Different conformations of the same molecule
Different molecules altogether (NOT isomers)
10. What is the systematic name of the molecule below?
a.
b.
c.
d.
e.
2,4-diethyl-3-heptanol
3-methyl-5-propyl-4-heptanol
5-methyl-3-propyl-4-heptanol
3-methyl-5-ethyl-4-octanol
None of the above.
11. The MAJOR product of the reaction below would be called:
a.
b.
c.
d.
e.
2-pentene
2-chloropentane
3-chloropentane
2,3-dichloropentane
2,3-dichloro-2-pentene
12. The MAJOR product of the reaction below would be called:
a. 1-methylcyclohexene
b. 1-bromo-2-methylcyclohexane
c. 1-bromo-1-methylcyclohexane
d. 2-bromo-1-methylcyclohexane
e. 1,2-dibromo-1-methylcyclohexane
13. The MAJOR product from the dehydration of the alcohol below would be:
a.
b.
c.
d.
14. In a hydrogenation reaction, the unsaturated fatty acid shown below is capable of reacting with how many hydrogen
molecules (H2)?
a. ½ H2 molecule
b. 1 H2 molecule
c. 2 H2 molecules
d. 4 H2 molecules
e. This compound can NOT be hydrogenated
15. Rank the fatty acids below from LOWEST melting point to HIGHEST melting point.
a.
b.
c.
d.
e.
2<3<1<4
1<4<3<2
3<1<4<2
3<4<2<1
1<3<2<4
16. True or False: The molecule below would likely be soluble in water.
a. TRUE
b. FALSE
17. Rank the compounds below from LOWEST melting point to HIGHEST melting point.
a.
b.
c.
d.
e.
1<2<3<4
1<2<4<3
2<1<3<4
2<1<4<3
2<4<1<3
18. The compound below with the HIGHEST solubility in water:
19. The ketone below could have been obtained from:
a.
b.
c.
d.
e.
the reduction of a primary alcohol
the oxidation of a primary alcohol
the oxidation of a secondary alcohol
the reduction of a secondary alcohol
the hydration of an alkene
20. Select the molecule below most likely to intercalate with DNA.
FREE RESPONSE QUESTIONS:
1.
(5 points) Write the skeletal formula for:
2,2,5,5-tetramethoxy-3-decyne
2.
(4 points) Draw the expanded structural formula for two constitutional isomers of cyclohexane.
3.
(6 points) Water-soluble vitamins dissolve easily in water, and are readily excreted from the body through the urinary
system. Fat-soluble vitamins are absorbed by the intestinal tract and can accumulate in adipose tissue (fat cells) due to
their solubility. For this reason, fat soluble vitamins generally pose a greater risk for toxicity when consumed in excess
(leading to hypervitaminosis).
Based on the structures of four vitamins below:
A) Circle the vitamins that are water-soluble.
B) Explain your reasoning & discuss why the other vitamins would not be soluble in water. Be sure to use the concepts
and terms behind molecular polarity & intermolecular forces to rationalize your choice.
4.
A. (4 points) Write the condensed structural formula for the alcohol that would have to be dehydrated to form the
alkene below.
B. (1 point) Classify the Alcohol as primary (1o), secondary (2o) or tertiary (3o).
BONUS: (5 POINTS)
Methyl methacrylate (shown below) is used in a variety of medical applications, including use as a cement in total hip replacements.
This monomer can also react in an alkene polymerization to yield polymethyl methyacrylate (PMMA), otherwise known as plexiglass.
Draw the product of polymerizing methyl methacrylate.