Transcript Organic Chemistry

Organic and Biochemical
Molecules
Chapter 21
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1. Classify the following compounds as saturated or unsaturated.
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2. What is the general formula for a hydrocarbon with one ring and a
triple bond?
a. CnH2n+2
b. CnH2n
c. CnH2n–2
d. CnH2n–4
e. CnH2n–6
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3. Draw the following alkanes:
a. 4-bromo-3,3-dimethylhexane
b. 3-ethyl-1-methyl-1-propylcyclopentane
c. 5-ethyl-2,2-difluoro-3-isopropylheptane
d. 4-butyl-1-chloro-1-ethylcyclohexane
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4. Name the following alkanes:
Cl
Br
Cl
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5. Draw the following alkenes:
a. 4,7-dibromo-3-propyl-2-heptene
b. 3,3-dipropylcyclobutene
c. trans-1,3-pentadiene
d. cis-2-chloro-5-ethyl-3-octene
Organic and Biochemical Molecules
Geometric isomers of alkenes – If each sp2 C has 2 different groups attached it
will have two possible orientations due the fact that pi bonds do not allow for
free rotation – If each sp2 C has only one hydrogen you can classify the
structure as cis or trans
F
H
Cl
H
H
Trans
2 Hydrogens are on
opposite sides
of pi bond
H
Cis
2 Hydrogens are on
the same side
of pi bond
Cl
F
Although these structures are
Geometric isomers (the 2 halogens
are on opposite sides in the left
structure and same side in the right)
you don’t refer to them as cis/trans
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6 . Name the following alkenes.
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7. Draw the following alkynes:
a. 3-ethyl-4,5-difluoro-1-pentyne
b. 7,7-dimethyl-2,4-octadiyne
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8. Name the following alkynes:
a.
b.
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9. For each of the following draw all of the structural isomers. Do any
of your structures have geometric isomers? If so, draw and label
them.
a. C6H14
b. C5H10
c. C4H6
d. C4H7Br
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10. Draw the following molecules.
a. para-iodoisobutylbenzene
b. meta-tert-butyltoluene
c. 2,4,6-tribromophenol
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11. Write out the reaction for the mono-chlorination of pentane. What
type of reaction is this?
Organic and Biochemical Molecules
12. Predict the product for the following addition reactions:
a. 1-pentene + Br2 
b. 2-butene + HCl 
c. 2-pentene + HBr 
d. 1-butene + H2O (in the pressence of H+) 
Organic and Biochemical Molecules
13. Which of the following transitions does not represent a
hydrogenation reaction?
a. 1-butene  butane
b. 1-pentyne  pentane
c. pentane  2-pentene
d. butanal  1-butanol
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14. Identify the functional groups that are present in the following
compounds:
aspartame
estrogen
vanillin
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15. For each of the following (1) draw the products of
oxidation and (2) name the reactants and products:
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16. Draw the following:
a. 4-bromo-3-ethylbutanoic acid
b. 6-chloro-3-hexanone
c. 2,3-dimethylpentanal
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17. Classify the following amines as primary, secondary or
tertiary;
a. tertbutylamine
e. ethylhexylamine
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18. Predict and name the products for the following:
a. propanoic acid + 3-methyl-1-butanol 
b. methanoic acid + 1-propanol 
c. 2,3-dibromohexanoic acid + ethanol 
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20. What compounds would you use to synthesize the
following esters?
a. methyl ethanoate
b. cyclohexyl propanoate
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21. Circle the chiral carbons in the following:
O
H
H
H
OH
OH
OH
OH
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22. Peptide bonds in proteins are the result of ___________
reactions between __________. Differentiate between
primary, secondary and tertiary structures of a protein? How
many possible dipeptides will result if you were to mix valine
and leucine together?
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23. Draw gly-phe-ser-ala
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24. What type of monomers are used to make addition
polymers?
a. Alkanes
b. Alkenes
c. Alcohols and carboxylic acids
d. Amines and carboxylic acids
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25. What type of monomers are used to make condensation
polymers?
a. Alkanes
b. Alkenes
c. Alcohols and carboxylic acids
d. Amines and carboxylic acids
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26. Draw a short segment of the polymer that is the result of the
following monomers:
a. tetrafluoroethene
b. 4-methyl-2-pentene
c. 1,1-dichloro-1-butene
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27. Draw the monomer used to make the following polymers.
a.
d.
b.
e.
c.
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28. Which of the following are examples of condensation polymers?
a. Proteins
b. DNA
c. Polysaccharides
d. Polystyrene
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1. Saturated => all single bonds
Unsaturated => double or triple bonds
2.
3.
a. 4-isopropyl-5-methyloctane
b. 2,5,5-trichloror-4-propylheptane
c. 2-bromo-4-isobutyl-1-methylcyclohexane
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4.
5. a. 4-fluoro-5-methyl-3-heptane
b. 3-chloro-1isopropylcyclohexene
c. cis-2-hexane
d. trans-8,8-dibromo-4-methyl-2-octene
e. 5,8-diethyl-1,7-decadiene
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6.
7.
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