Write the chemical formula and Lewis structure of the following, each of which contains five carbon atoms:
(a) an alkane
(b) an alkene
(c) an alkyne
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Chemistry 2e · 20.1 Hydrocarbons
15 problems from the book, with its answers. Check your working, or have any of them explained to you on the whiteboard.
Exercises 1
Write the chemical formula and Lewis structure of the following, each of which contains five carbon atoms:
(a) an alkane
(b) an alkene
(c) an alkyne
Exercises 3
Exercises 5
Exercises 7
Exercises 9
Exercises 11
Exercises 13
Exercises 15
Exercises 17
Exercises 19
Exercises 21
Exercises 23
Exercises 25
Exercises 27
Exercises 29
The tutor teaches the whole section, drawing it out step by step and answering your questions as you go.
On a microscopic level, how does the reaction of bromine with a saturated hydrocarbon differ from its reaction with an unsaturated hydrocarbon? How are they similar?
Explain why unbranched alkenes can form geometric isomers while unbranched alkanes cannot. Does this explanation involve the macroscopic domain or the microscopic domain?
Explain why these two molecules are not isomers:

Write the Lewis structure and molecular formula for each of the following hydrocarbons:
(a) hexane
(b) 3-methylpentane
(c) cis-3-hexene
(d) 4-methyl-1-pentene
(e) 3-hexyne
(f) 4-methyl-2-pentyne
Give the complete IUPAC name for each of the following compounds:
(a) CH₃CH₂CBr₂CH₃
(b) (CH₃)₃CCl
(c)

(d)

(e)

(f)

(g)
Butane is used as a fuel in disposable lighters. Write the Lewis structure for each isomer of butane.
Write Lewis structures for the cis–trans isomers of
Isooctane is the common name of the isomer of C₈H₁₈ used as the standard of 100 for the gasoline octane rating:

(a) What is the IUPAC name for the compound?
(b) Name the other isomers that contain a five-carbon chain with three methyl substituents.
Write Lewis structures and IUPAC names for all isomers of C₄H₉Cl.
Write the structures for all the isomers of the –C₅H₁₁ alkyl group.
Benzene is one of the compounds used as an octane enhancer in unleaded gasoline. It is manufactured by the catalytic conversion of acetylene to benzene:
Draw Lewis structures for these compounds, with resonance structures as appropriate, and determine the hybridization of the carbon atoms in each.
Write two complete, balanced equations for each of the following reactions, one using condensed formulas and one using Lewis structures.
(a) 1 mol of 1-butyne reacts with 2 mol of iodine.
(b) Pentane is burned in air.
What mass of 2-bromopropane could be prepared from 25.5 g of propene? Assume a 100% yield of product.
Ethylene can be produced by the pyrolysis of ethane:
How many kilograms of ethylene is produced by the pyrolysis of 1.000 10³ kg of ethane, assuming a 100.0% yield?