© 2016 Pearson Education, Inc.General, Organic, and Biological Chemistry: Structures of Life, 5/e Karen C.. © 2016 Pearson Education, Inc.General, Organic, and Biological Chemistry: Stru
Trang 1© 2016 Pearson Education, Inc.
General, Organic, and Biological Chemistry: Structures of Life, 5/e
Karen C Timberlake
Solution
a Many organic compounds are not soluble in water.
b Inorganic compounds are more likely to have high melting points.
c Organic compounds are more likely to be flammable.
Study Check 12.1
What elements are always found in organic compounds?
Answer
C and H
Indicate whether the following properties are more typical of organic or inorganic compounds:
a is not soluble in water
b has a high melting point
c burns in air
Sample Problem 12.1 Properties of Organic Compounds
Trang 2© 2016 Pearson Education, Inc.
General, Organic, and Biological Chemistry: Structures of Life, 5/e
Karen C Timberlake
Solution
Step 1 Draw the carbon chain A molecule of pentane has five carbon atoms in a continuous chain
Step 2 Draw the expanded structural formula by adding the hydrogen atoms using single bonds to each of the
carbon atoms
Step 3 Draw the condensed structural formula by combining the H atoms with each C atom
Draw the expanded, condensed, and line-angle structural formulas for pentane
Sample Problem 12.2 Drawing Expanded, Condensed, and
Line-Angle Structural Formulas for an Alkane
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General, Organic, and Biological Chemistry: Structures of Life, 5/e
Sample Problem 12.2 Drawing Expanded, Condensed, and
Line-Angle Structural Formulas for an Alkane
Trang 4© 2016 Pearson Education, Inc.
General, Organic, and Biological Chemistry: Structures of Life, 5/e
Karen C Timberlake
Solution
a A chain with eight carbon atoms is octane.
b The ring of six carbon atoms is named cyclohexane.
Trang 5© 2016 Pearson Education, Inc.
General, Organic, and Biological Chemistry: Structures of Life, 5/e
Karen C Timberlake
Solution
a When we add up the number of C atoms and H atoms, they give the same molecular formula C4H10 The condensed structural formula on the left has a chain of four C atoms Even though the —CH3 ends are drawn up, they are part
of the four-carbon chain The condensed structural formula on the right also has a four-carbon chain even though one
—CH3 end is drawn down Thus both condensed structural formulas represent the same molecule and are not
structural isomers
b When we add up the number of C atoms and H atoms, they give the same molecular formula C6H14 The line-angle structural formula on the left has a five-carbon chain with a —CH3 substituent on the second carbon of the chain The line-angle structural formula on the right has a four-carbon chain with two —CH3 substituents, one bonded to the second carbon and one bonded to the third carbon Thus there is a different order of bonding of atoms, which
represents structural isomers
Identify each pair of formulas as structural isomers or the same molecule
Sample Problem 12.4 Structural Isomers
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General, Organic, and Biological Chemistry: Structures of Life, 5/e
Trang 7© 2016 Pearson Education, Inc.
General, Organic, and Biological Chemistry: Structures of Life, 5/e
Karen C Timberlake
Solution
Step 1 Write the alkane name for the longest chain of carbon atoms
Give the IUPAC name for the following alkane:
Sample Problem 12.5 Writing IUPAC Names for Alkanes with
Substituents
Trang 8© 2016 Pearson Education, Inc.
General, Organic, and Biological Chemistry: Structures of Life, 5/e
Karen C Timberlake
Step 2 Number the carbon atoms starting from the end nearer a substituent Carbon 1 is the carbon atom nearer a
methyl group, —CH3, on the left
Step 3 Give the location and name for each substituent (alphabetical order) as a prefix to the name of the main
chain The substituents, which are bromo and methyl groups, are listed in alphabetical order (bromo first, then methyl) A hyphen is placed between the number on the carbon chain and the substituent name When
there are two or more of the same substituent, a prefix (di, tri, tetra) is used in front of the name However,
these prefixes are not used to determine the alphabetical order of the substituents Then commas are used to separate the numbers for the locations of the substituents
Continued
Sample Problem 12.5 Writing IUPAC Names for Alkanes with
Substituents
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General, Organic, and Biological Chemistry: Structures of Life, 5/e
Trang 10© 2016 Pearson Education, Inc.
General, Organic, and Biological Chemistry: Structures of Life, 5/e
Karen C Timberlake
Solution
Step 1 Draw the main chain of carbon atoms For butane, we draw a chain or a zigzag line of four carbon atoms
Step 2 Number the chain and place the substituents on the carbons indicated by the numbers The first part of the
name indicates two methyl groups —CH3: one on carbon 2 and one on carbon 3
Draw the condensed and line-angle structural formulas for 2,3-dimethylbutane
Sample Problem 12.6 Drawing Condensed Structures from
IUPAC Names
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General, Organic, and Biological Chemistry: Structures of Life, 5/e
Trang 12© 2016 Pearson Education, Inc.
General, Organic, and Biological Chemistry: Structures of Life, 5/e
Karen C Timberlake
Solution
a.
Step 1 Name the longest carbon chain that contains the double bond There are five carbon atoms in the longest
carbon chain containing the double bond Replace the ane in the corresponding alkane name with ene to
Trang 13© 2016 Pearson Education, Inc.
General, Organic, and Biological Chemistry: Structures of Life, 5/e
Karen C Timberlake
Step 2 Number the carbon chain starting from the end nearer the double bond Place the number of the first
carbon in the double bond in front of the alkene name
Alkenes or alkynes with two or three carbons do not need numbers For example, the double bond in ethene or propene must be between carbon 1 and carbon 2
Step 3 Give the location and name for each substituent (alphabetical order) as a prefix to the alkene name The
methyl group is located on carbon 4
Continued
Sample Problem 12.7 Naming Alkenes and Alkynes
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General, Organic, and Biological Chemistry: Structures of Life, 5/e
Karen C Timberlake
b.
Step 1 Name the longest carbon chain that contains the triple bond There are six carbon atoms in the longest chain
containing the triple bond Replace the ane in the corresponding alkane name with yne to give hexyne.
Step 2 Number the carbon chain starting from the end nearer the triple bond Place the number of the first carbon in
the triple bond in front of the alkyne name
Step 3 Give the location and name for each substituent (alphabetical order) as a prefix to the alkyne name There are
no substituents in this formula
Continued
Sample Problem 12.7 Naming Alkenes and Alkynes
Trang 15© 2016 Pearson Education, Inc.
General, Organic, and Biological Chemistry: Structures of Life, 5/e
Trang 16© 2016 Pearson Education, Inc.
General, Organic, and Biological Chemistry: Structures of Life, 5/e
Karen C Timberlake
Solution
a This is a cis isomer because the two halogen atoms attached to the carbon atoms of the double bond are on the same
side The name of the two-carbon alkene, starting with the bromo group on carbon 1, is cis-1-bromo-2-chloroethene.
b This is a trans isomer because the two alkyl groups attached to the carbon atoms of the double bond are on opposite
sides of the double bond This isomer of the five-carbon alkene, 2-pentene, is named trans-2-pentene.
Trang 17© 2016 Pearson Education, Inc.
General, Organic, and Biological Chemistry: Structures of Life, 5/e
Trang 18© 2016 Pearson Education, Inc.
General, Organic, and Biological Chemistry: Structures of Life, 5/e
Karen C Timberlake
Solution
In an addition reaction, hydrogen adds to the double bond to give an alkane
For an asymmetrical alkene, the H— from water (H —OH) adds to the carbon with the greater number of hydrogen
atoms, and the —OH bonds to the carbon with fewer H atoms
Draw the condensed structural formula for the product that forms in the following hydration reaction:
Sample Problem 12.10 Hydration
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General, Organic, and Biological Chemistry: Structures of Life, 5/e
Trang 20© 2016 Pearson Education, Inc.
General, Organic, and Biological Chemistry: Structures of Life, 5/e
A firefighter/EMT arrives at a home where a premature baby has been delivered To prevent hypothermia during
transport to the neonatal facility, she wraps the baby in cling wrap Draw and name the monomer unit and draw a
portion of the polymer formed from three monomer units for cling wrap, which is polydichloroethylene (ethene)
Sample Problem 12.11 Polymers
Trang 21© 2016 Pearson Education, Inc.
General, Organic, and Biological Chemistry: Structures of Life, 5/e
Give the IUPAC name for the following:
Sample Problem 12.12 Naming Aromatic Compounds