CH 223

Chapter 20 Study Guide

Alkanes, Cycloalkanes, Unsaturated Hydrocarbons, and Isomers

1. Explain and apply what an alkane is, and how changes to alkane structures produce different
types of hydrocarbons
a. Alkanes are hydrocarbons with only C-C single bonds
b. In an alkane, the geometry of all the carbon atoms is tetrahedral (both electron and
molecular)
c. Prototypical alkanes are straight carbon chains, but they may be branched
d. If the ends of an alkane are joined by a bond, the resulting molecule is known as a
cycloalkane (Note that cycloalkanes have two fewer hydrogen atoms)

2. Explain and apply what alkenes and alkynes are, and how double and triple bonds change
molecular structure
a. Alkenes are hydrocarbons with at least one C=C double bond
b. In the double-bonded carbons of an alkene, the electron and molecular geometries are
trigonal planar
c. Alkynes are hydrocarbons with at least one C≡C triple bond
d. In the triple-bonded carbons of an alkyne, the electron and molecular geometries are
linear

3. Explain and apply what isomers are, the difference between isomers and conformers, and the
different types of isomer
a. Isomers are compounds with the same formula but a different chemical identity.
Conformers have the same chemical identity, but are simply in a different shape
b. Structural isomers have different connectivity – that is, atoms are connected in different
ways
c. Geometric isomers have the same connectivity – that is, the same atoms are connected
to each other – but the bonds have a different arrangement in space.
d. Practice Problems: 20.6

Drawing Hydrocarbon Structures

1. Fluently represent molecules as either full structural drawings or line angle drawings
a. Full structural drawings represent all the bonds in a molecule, including their geometric
isomerism
b. Line angle drawings represent bonds as lines. These lines connect points which
represent carbon atoms, occurring at the ends or meeting points of those lines. The
atomic symbol for carbon (C) is not drawn explicitly, and hydrogen atoms are omitted
altogether (they are implied). Heteroatoms and any H atoms they carry are drawn in.
Naming and Drawing Organic Molecules

1. Name a hydrocarbon molecule based on its structure, or draw it based on its name
a. Hydrocarbons are named based on the longest chain of carbon atoms in the molecule
b. Branches are named as alkyl groups (methyl, ethyl, etc.) and their location is designated
by locants (numbers)
c. Locants can also be used to designate the positions of double and triple bonds, halogen
atoms (F, Cl, Br, I) or other moieties (OH groups, NH2 groups, etc.)
d. Practice Problems: 20.10, 20.12, 20.19

Functional Groups

1. Accurately identify or draw examples of the various functional groups in organic molecules, and
name simple molecules containing certain functional groups
a. You should be able to identify and draw alcohols, ethers, aldehydes, ketones, esters,
amides, carboxylic acids, and amines
b. See summary table on p. 1013
c. Practice Problems: 20.36, 20.38

Organic Reactions

1. Classify chemical reactions by type, and draw the products of a reaction given its type and
reactants
a. Dehydration synthesis reactions remove water, joining two molecules together
i. carboxylic acid + alcohol → ester
ii. carboxylic acid + amine → amide
b. Hydrolysis reactions reverse dehydration synthesis reactions, inserting water and splitting
a molecule in two
c. Oxidation reactions increase the number of oxygen atoms a carbon is bonded to
i. alkane → alcohol → aldehyde/ketone → carboxylic acid/ester
d. Reduction reactions reverse oxidation reactions
e. Hydrogenation reactions use hydrogen to transform alkynes into alkenes and alkenes
into alkanes