Name: _____________________________________
Date: _________________________________
CHEM 1307: Group Work 11 – Chapter 11 (88 pts)
The Unsaturated Hydrocarbons
Please write legibly. Credit will not be given for illegible responses.
Problem 1: (4 pts)
Draw a condensed formula for each of the following compounds:
a) 2-hexyne
b) 4-methyl-1-pentyne
c) 1-chloro-4,4,5-trimethyl-2-heptyne
d) 2-bromo-3-chloro-7,8-dimethyl-4-decyne
Problem 2: (4 pts)
Name each of the following using I.U.P.A.C. Nomenclature System:
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Problem 3: (3 pts)
Draw each of the following compounds using condensed formulas:
a) 3,3,5-trimethyl-1-hexene
b) 1-bromo-3-chloro-1-heptyne
c) 3-heptyne
Problem 4: (11 pts)
Which of the following can exist as cis- and trans- isomers? Draw and name all the cis- and trans- isomers.
a) H2C=CH2
b) CH3CH=CHCH3
c) Cl2C=CBr2
d) ClBrC=CClBr
e) (CH3)2C=C(CH3)2
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Problem 5: (4 pts)
Write a balanced equation for each of the following reactions:
a) 1,4-pentadiene + H2
b) 3-methyl-1,4-cyclohexadiene + Cl2
c) 2,4-heptadiene + Br2
d) 3-methylcyclopentene + H2O with acid (H+) catalysis
Problem 6: (4 pts)
Draw and name the product in each of the following reactions:
a) cyclopentene + H2O (H+)
b) cyclopentene + HCl
c) cyclopentene + H2
d) cyclopentene + HI
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Problem 7: (4 pts)
Write a balanced equation for each of the following reactions:
a) hydration of 1-butyne
b) hydration of 2-butyne
Problem 8: (6 pts)
Provide the I.U.P.A.C. name for each of the following molecules. Write a balanced equation for the
monohydration of each.
Problem 8: (4 pts)
Draw each of the following compounds, using condensed formulas:
a) p-xylene
b) isopropylbenzene
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c) m-nitroanisole
d) p-methylbenzaldehyde
Problem 9: (10 pts)
Which of the following structures have incorrect I.U.P.A.C. names? If incorrect, give the correct I.U.P.A.C.
name.
Problem 10: (3 pts)
Triple bonds react in a manner analogous to that of double bonds. The extra pair of electrons in the triple bond,
however, generally allows 2 mol of a given reactant to add to add to the triple bond in contrast to 1 mol with
the double bond. The “rich get richer” rule holds. Predict the major product in each of the following reactions:
a) Acetylene with 2 mol HCl
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b) Propyne with 2 mol HBr
c) 2-Butyne with 2 mol HI
Problem 11: (12 pts)
Predict the major product in each of the following reactions. Name the alkene reactant and the product, using
I.U.P.A.C. nomenclature.
Problem 12: (4 pts)
Name each of the following compounds, using the I.U.P.A.C. system.
Problem 13: (6 pts)
Draw all of the products that could be formed in a reaction of benzene with each of the following:
a) 2Cl2 in the presence of FeCl3
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b) 2SO3 in the presence of concentrated sulfuric acid
c) 2HNO3 in the presence of concentrated sulfuric acid
Problem 14: (5 pts)
Draw the following molecule. Create a chain of 5 sequential carbons. On the second carbon, attach an ethyl
group. On the 3rd carbon, attach a propyl group. Also on the 3rd carbon, attach an ethyl group. On the 4th
carbon, attach two methyl groups. Finally, place a double bond on the first carbon and a single bond on all the
remaining carbons.
Name the molecule, using the I.U.P.A.C. system.
Problem 15: (4 pts)
Draw the following molecule. Create a chain of 5 sequential carbons. On the second carbon, attach an ethyl
group. On the 3rd carbon, attach a propyl group. Also on the 3rd carbon, attach an ethyl group. Finally, place a
triple bond connecting C(4) and C(5), and a single bond on all the remaining carbons.
Name the molecule, using the I.U.P.A.C. system.
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