Saturated Hydrocarbons Section 20.1 Steven S. Zumdahl Susan A. Zumdahl Donald J. DeCoste Gretchen M....
-
Upload
horatio-grant -
Category
Documents
-
view
223 -
download
0
Transcript of Saturated Hydrocarbons Section 20.1 Steven S. Zumdahl Susan A. Zumdahl Donald J. DeCoste Gretchen M....
![Page 1: Saturated Hydrocarbons Section 20.1 Steven S. Zumdahl Susan A. Zumdahl Donald J. DeCoste Gretchen M. Adams University of Illinois at Urbana-Champaign Chapter.](https://reader036.fdocuments.in/reader036/viewer/2022062301/56649e4d5503460f94b42c16/html5/thumbnails/1.jpg)
Saturated Hydrocarbons
Section 20.1
Steven S. Zumdahl
Susan A. Zumdahl
Donald J. DeCoste
Gretchen M. Adams • University of Illinois at Urbana-Champaign
Chapter 20
Organic Chemistry
![Page 2: Saturated Hydrocarbons Section 20.1 Steven S. Zumdahl Susan A. Zumdahl Donald J. DeCoste Gretchen M. Adams University of Illinois at Urbana-Champaign Chapter.](https://reader036.fdocuments.in/reader036/viewer/2022062301/56649e4d5503460f94b42c16/html5/thumbnails/2.jpg)
Saturated Hydrocarbons
Section 20.1
1. To understand the types of bonds formed by the carbon atom
2. To learn about the alkanes
3. To learn about structural isomers
4. To learn to draw structural formulas
5. To learn to name alkanes and substituted alkanes
6. To learn about the composition and uses of petroleum
7. To learn about the chemical reactions of alkanes
Objectives
![Page 3: Saturated Hydrocarbons Section 20.1 Steven S. Zumdahl Susan A. Zumdahl Donald J. DeCoste Gretchen M. Adams University of Illinois at Urbana-Champaign Chapter.](https://reader036.fdocuments.in/reader036/viewer/2022062301/56649e4d5503460f94b42c16/html5/thumbnails/3.jpg)
Saturated Hydrocarbons
Section 20.1
Carbon Chemistry
• Carbon is unusual. Bonds strongly to itself Forms long chains or rings
• Biomolecule – molecule that functions in maintaining and reproducing life
• Organic compounds – vast majority of carbon compounds Exceptions – oxides and carbonates
![Page 4: Saturated Hydrocarbons Section 20.1 Steven S. Zumdahl Susan A. Zumdahl Donald J. DeCoste Gretchen M. Adams University of Illinois at Urbana-Champaign Chapter.](https://reader036.fdocuments.in/reader036/viewer/2022062301/56649e4d5503460f94b42c16/html5/thumbnails/4.jpg)
Saturated Hydrocarbons
Section 20.1
A. Carbon Bonding
• When carbon has 4 atoms bound to it, these atoms have a tetrahedral shape.
![Page 5: Saturated Hydrocarbons Section 20.1 Steven S. Zumdahl Susan A. Zumdahl Donald J. DeCoste Gretchen M. Adams University of Illinois at Urbana-Champaign Chapter.](https://reader036.fdocuments.in/reader036/viewer/2022062301/56649e4d5503460f94b42c16/html5/thumbnails/5.jpg)
Saturated Hydrocarbons
Section 20.1
A. Carbon Bonding
Double bond
Triple bond • Sharing of 3 pairs of electrons
• Sharing of 2 pairs of electrons
![Page 6: Saturated Hydrocarbons Section 20.1 Steven S. Zumdahl Susan A. Zumdahl Donald J. DeCoste Gretchen M. Adams University of Illinois at Urbana-Champaign Chapter.](https://reader036.fdocuments.in/reader036/viewer/2022062301/56649e4d5503460f94b42c16/html5/thumbnails/6.jpg)
Saturated Hydrocarbons
Section 20.1
B. Alkanes
• Hydrocarbons – compounds composed of carbon and hydrogen Saturated – all carbon-carbon bonds are single bonds Unsaturated – containing carbon-carbon multiple bonds
![Page 7: Saturated Hydrocarbons Section 20.1 Steven S. Zumdahl Susan A. Zumdahl Donald J. DeCoste Gretchen M. Adams University of Illinois at Urbana-Champaign Chapter.](https://reader036.fdocuments.in/reader036/viewer/2022062301/56649e4d5503460f94b42c16/html5/thumbnails/7.jpg)
Saturated Hydrocarbons
Section 20.1
B. Alkanes
• Alkanes – saturated hydrocarbons
![Page 8: Saturated Hydrocarbons Section 20.1 Steven S. Zumdahl Susan A. Zumdahl Donald J. DeCoste Gretchen M. Adams University of Illinois at Urbana-Champaign Chapter.](https://reader036.fdocuments.in/reader036/viewer/2022062301/56649e4d5503460f94b42c16/html5/thumbnails/8.jpg)
Saturated Hydrocarbons
Section 20.1
B. Alkanes
• Normal, straight-chain or unbranched hydrocarbons
• Contain strings or chains of carbon atoms Representations
![Page 9: Saturated Hydrocarbons Section 20.1 Steven S. Zumdahl Susan A. Zumdahl Donald J. DeCoste Gretchen M. Adams University of Illinois at Urbana-Champaign Chapter.](https://reader036.fdocuments.in/reader036/viewer/2022062301/56649e4d5503460f94b42c16/html5/thumbnails/9.jpg)
Saturated Hydrocarbons
Section 20.1
B. Alkanes
![Page 10: Saturated Hydrocarbons Section 20.1 Steven S. Zumdahl Susan A. Zumdahl Donald J. DeCoste Gretchen M. Adams University of Illinois at Urbana-Champaign Chapter.](https://reader036.fdocuments.in/reader036/viewer/2022062301/56649e4d5503460f94b42c16/html5/thumbnails/10.jpg)
Saturated Hydrocarbons
Section 20.1
C. Structural Formulas and Isomerism
• Structural isomerism – occurs when 2 molecules have the same atoms but different bonds
![Page 11: Saturated Hydrocarbons Section 20.1 Steven S. Zumdahl Susan A. Zumdahl Donald J. DeCoste Gretchen M. Adams University of Illinois at Urbana-Champaign Chapter.](https://reader036.fdocuments.in/reader036/viewer/2022062301/56649e4d5503460f94b42c16/html5/thumbnails/11.jpg)
Saturated Hydrocarbons
Section 20.1
D. Naming Alkanes
• The name for an alkane is based on Greek root with the suffix –ane.
Basic principles
![Page 12: Saturated Hydrocarbons Section 20.1 Steven S. Zumdahl Susan A. Zumdahl Donald J. DeCoste Gretchen M. Adams University of Illinois at Urbana-Champaign Chapter.](https://reader036.fdocuments.in/reader036/viewer/2022062301/56649e4d5503460f94b42c16/html5/thumbnails/12.jpg)
Saturated Hydrocarbons
Section 20.1
D. Naming Alkanes
• For branched hydrocarbons use the longest continuous chain for the root name.
Basic principles
![Page 13: Saturated Hydrocarbons Section 20.1 Steven S. Zumdahl Susan A. Zumdahl Donald J. DeCoste Gretchen M. Adams University of Illinois at Urbana-Champaign Chapter.](https://reader036.fdocuments.in/reader036/viewer/2022062301/56649e4d5503460f94b42c16/html5/thumbnails/13.jpg)
Saturated Hydrocarbons
Section 20.1
D. Naming Alkanes
• Alkanes missing one H atom can have another hydrocarbon attached at the missing H point.
Basic principles
![Page 14: Saturated Hydrocarbons Section 20.1 Steven S. Zumdahl Susan A. Zumdahl Donald J. DeCoste Gretchen M. Adams University of Illinois at Urbana-Champaign Chapter.](https://reader036.fdocuments.in/reader036/viewer/2022062301/56649e4d5503460f94b42c16/html5/thumbnails/14.jpg)
Saturated Hydrocarbons
Section 20.1
D. Naming Alkanes
• Specify the names of substituents by numbering the C atoms starting at the end closest to the branching.
Basic principles
![Page 15: Saturated Hydrocarbons Section 20.1 Steven S. Zumdahl Susan A. Zumdahl Donald J. DeCoste Gretchen M. Adams University of Illinois at Urbana-Champaign Chapter.](https://reader036.fdocuments.in/reader036/viewer/2022062301/56649e4d5503460f94b42c16/html5/thumbnails/15.jpg)
Saturated Hydrocarbons
Section 20.1
D. Naming Alkanes
Basic principles
![Page 16: Saturated Hydrocarbons Section 20.1 Steven S. Zumdahl Susan A. Zumdahl Donald J. DeCoste Gretchen M. Adams University of Illinois at Urbana-Champaign Chapter.](https://reader036.fdocuments.in/reader036/viewer/2022062301/56649e4d5503460f94b42c16/html5/thumbnails/16.jpg)
Saturated Hydrocarbons
Section 20.1
D. Naming Alkanes
• If a substituent occurs more than once, use a prefix to show this.
Basic principles
2,3-dimethylpentane
![Page 17: Saturated Hydrocarbons Section 20.1 Steven S. Zumdahl Susan A. Zumdahl Donald J. DeCoste Gretchen M. Adams University of Illinois at Urbana-Champaign Chapter.](https://reader036.fdocuments.in/reader036/viewer/2022062301/56649e4d5503460f94b42c16/html5/thumbnails/17.jpg)
Saturated Hydrocarbons
Section 20.1
D. Naming Alkanes
![Page 18: Saturated Hydrocarbons Section 20.1 Steven S. Zumdahl Susan A. Zumdahl Donald J. DeCoste Gretchen M. Adams University of Illinois at Urbana-Champaign Chapter.](https://reader036.fdocuments.in/reader036/viewer/2022062301/56649e4d5503460f94b42c16/html5/thumbnails/18.jpg)
Saturated Hydrocarbons
Section 20.1
Exercise
Name each of the following:
a)
2,2,4,5-tetramethylhexane
b)
3,6-diethyl-3-methyloctane
![Page 19: Saturated Hydrocarbons Section 20.1 Steven S. Zumdahl Susan A. Zumdahl Donald J. DeCoste Gretchen M. Adams University of Illinois at Urbana-Champaign Chapter.](https://reader036.fdocuments.in/reader036/viewer/2022062301/56649e4d5503460f94b42c16/html5/thumbnails/19.jpg)
Saturated Hydrocarbons
Section 20.1
E. Petroleum
• Hydrocarbons are an energy resource.
![Page 20: Saturated Hydrocarbons Section 20.1 Steven S. Zumdahl Susan A. Zumdahl Donald J. DeCoste Gretchen M. Adams University of Illinois at Urbana-Champaign Chapter.](https://reader036.fdocuments.in/reader036/viewer/2022062301/56649e4d5503460f94b42c16/html5/thumbnails/20.jpg)
Saturated Hydrocarbons
Section 20.1
E. Petroleum
• Petroleum – thick, dark liquid composed mostly of hydrocarbon compounds
• Natural gas – consists mostly of methane, usually associated with petroleum deposits
![Page 21: Saturated Hydrocarbons Section 20.1 Steven S. Zumdahl Susan A. Zumdahl Donald J. DeCoste Gretchen M. Adams University of Illinois at Urbana-Champaign Chapter.](https://reader036.fdocuments.in/reader036/viewer/2022062301/56649e4d5503460f94b42c16/html5/thumbnails/21.jpg)
Saturated Hydrocarbons
Section 20.1
F. Reactions of Alkanes
• Combustion – reaction with oxygen
• Substitution – one or more H atoms are replaced with different atoms
![Page 22: Saturated Hydrocarbons Section 20.1 Steven S. Zumdahl Susan A. Zumdahl Donald J. DeCoste Gretchen M. Adams University of Illinois at Urbana-Champaign Chapter.](https://reader036.fdocuments.in/reader036/viewer/2022062301/56649e4d5503460f94b42c16/html5/thumbnails/22.jpg)
Saturated Hydrocarbons
Section 20.1
F. Reactions of Alkanes
• Dehydrogenation – one or more H atoms are removed and the product is an unsaturated hydrocarbon
![Page 23: Saturated Hydrocarbons Section 20.1 Steven S. Zumdahl Susan A. Zumdahl Donald J. DeCoste Gretchen M. Adams University of Illinois at Urbana-Champaign Chapter.](https://reader036.fdocuments.in/reader036/viewer/2022062301/56649e4d5503460f94b42c16/html5/thumbnails/23.jpg)
Section 20.2
Unsaturated Hydrocarbons
1. To learn to name hydrocarbons with double and triple bonds
2. To understand addition reactions
3. To learn about the aromatic hydrocarbons
4. To learn to name aromatic compounds
Objectives
![Page 24: Saturated Hydrocarbons Section 20.1 Steven S. Zumdahl Susan A. Zumdahl Donald J. DeCoste Gretchen M. Adams University of Illinois at Urbana-Champaign Chapter.](https://reader036.fdocuments.in/reader036/viewer/2022062301/56649e4d5503460f94b42c16/html5/thumbnails/24.jpg)
Section 20.2
Unsaturated Hydrocarbons
A. Alkenes and Alkynes
• Alkenes – hydrocarbon containing carbon-carbon double bonds General formula CnH2n
• Alkynes – hydrocarbons containing carbon-carbon triple bonds General formula CnH2n – 2
![Page 25: Saturated Hydrocarbons Section 20.1 Steven S. Zumdahl Susan A. Zumdahl Donald J. DeCoste Gretchen M. Adams University of Illinois at Urbana-Champaign Chapter.](https://reader036.fdocuments.in/reader036/viewer/2022062301/56649e4d5503460f94b42c16/html5/thumbnails/25.jpg)
Section 20.2
Unsaturated Hydrocarbons
A. Alkenes and Alkynes
![Page 26: Saturated Hydrocarbons Section 20.1 Steven S. Zumdahl Susan A. Zumdahl Donald J. DeCoste Gretchen M. Adams University of Illinois at Urbana-Champaign Chapter.](https://reader036.fdocuments.in/reader036/viewer/2022062301/56649e4d5503460f94b42c16/html5/thumbnails/26.jpg)
Section 20.2
Unsaturated Hydrocarbons
Exercise
Name each of the following:
a)
2,3,5-trimethyl-2-hexene
b)
6-ethyl-3-methyl-3-octene
![Page 27: Saturated Hydrocarbons Section 20.1 Steven S. Zumdahl Susan A. Zumdahl Donald J. DeCoste Gretchen M. Adams University of Illinois at Urbana-Champaign Chapter.](https://reader036.fdocuments.in/reader036/viewer/2022062301/56649e4d5503460f94b42c16/html5/thumbnails/27.jpg)
Section 20.2
Unsaturated Hydrocarbons
• Addition reactions – new atoms form single bonds to the carbons formerly involved in a double or triple bond Hydrogenation – use H2 as the reactant to be added
Reactions of Alkenes
Halogenation – addition of halogen atoms
• Polymerization – joining of many small molecules to form a large molecule
A. Alkenes and Alkynes
![Page 28: Saturated Hydrocarbons Section 20.1 Steven S. Zumdahl Susan A. Zumdahl Donald J. DeCoste Gretchen M. Adams University of Illinois at Urbana-Champaign Chapter.](https://reader036.fdocuments.in/reader036/viewer/2022062301/56649e4d5503460f94b42c16/html5/thumbnails/28.jpg)
Section 20.2
Unsaturated Hydrocarbons
B. Aromatic Hydrocarbons
• Aromatic hydrocarbons – cyclic unsaturated hydrocarbons with strong aromas
![Page 29: Saturated Hydrocarbons Section 20.1 Steven S. Zumdahl Susan A. Zumdahl Donald J. DeCoste Gretchen M. Adams University of Illinois at Urbana-Champaign Chapter.](https://reader036.fdocuments.in/reader036/viewer/2022062301/56649e4d5503460f94b42c16/html5/thumbnails/29.jpg)
Section 20.2
Unsaturated Hydrocarbons
B. Aromatic Hydrocarbons
• Benzene – simplest aromatic hydrocarbon
![Page 30: Saturated Hydrocarbons Section 20.1 Steven S. Zumdahl Susan A. Zumdahl Donald J. DeCoste Gretchen M. Adams University of Illinois at Urbana-Champaign Chapter.](https://reader036.fdocuments.in/reader036/viewer/2022062301/56649e4d5503460f94b42c16/html5/thumbnails/30.jpg)
Section 20.2
Unsaturated Hydrocarbons
C. Naming Aromatic Compounds
• Monosubstituted benzenes –
use the substituent name as
a prefix of benzene
![Page 31: Saturated Hydrocarbons Section 20.1 Steven S. Zumdahl Susan A. Zumdahl Donald J. DeCoste Gretchen M. Adams University of Illinois at Urbana-Champaign Chapter.](https://reader036.fdocuments.in/reader036/viewer/2022062301/56649e4d5503460f94b42c16/html5/thumbnails/31.jpg)
Section 20.2
Unsaturated Hydrocarbons
C. Naming Aromatic Compounds
• Disubstituted benzenes Use numbers to
indicate the position of substituents and the substituent name as a prefix of benzene.
![Page 32: Saturated Hydrocarbons Section 20.1 Steven S. Zumdahl Susan A. Zumdahl Donald J. DeCoste Gretchen M. Adams University of Illinois at Urbana-Champaign Chapter.](https://reader036.fdocuments.in/reader036/viewer/2022062301/56649e4d5503460f94b42c16/html5/thumbnails/32.jpg)
Section 20.2
Unsaturated Hydrocarbons
C. Naming Aromatic Compounds
• Complex aromatic molecules
![Page 33: Saturated Hydrocarbons Section 20.1 Steven S. Zumdahl Susan A. Zumdahl Donald J. DeCoste Gretchen M. Adams University of Illinois at Urbana-Champaign Chapter.](https://reader036.fdocuments.in/reader036/viewer/2022062301/56649e4d5503460f94b42c16/html5/thumbnails/33.jpg)
Section 20.2
Unsaturated Hydrocarbons
Benzene as a side group is called phenyl
• Phenyl (phenyl group): A portion of a molecular structure which is equivalent to benzene minus one hydrogen atom: -C6H5
Chlorobenzene or Phenyl chloride
![Page 34: Saturated Hydrocarbons Section 20.1 Steven S. Zumdahl Susan A. Zumdahl Donald J. DeCoste Gretchen M. Adams University of Illinois at Urbana-Champaign Chapter.](https://reader036.fdocuments.in/reader036/viewer/2022062301/56649e4d5503460f94b42c16/html5/thumbnails/34.jpg)
Section 20.3
Introduction to Functional Groups and Alcohols
1. To learn the common functional groups in organic molecules
2. To learn about simple alcohols and how to name them
3. To learn about how some alcohols are made and used
4. To learn about simple ethers and how to name them
Objectives
![Page 35: Saturated Hydrocarbons Section 20.1 Steven S. Zumdahl Susan A. Zumdahl Donald J. DeCoste Gretchen M. Adams University of Illinois at Urbana-Champaign Chapter.](https://reader036.fdocuments.in/reader036/viewer/2022062301/56649e4d5503460f94b42c16/html5/thumbnails/35.jpg)
Section 20.3
Introduction to Functional Groups and Alcohols
A. Functional Groups • Functional group – additional atom or groups of atoms
(containing elements in addition to H and C) found on a mostly hydrocarbon molecule
![Page 36: Saturated Hydrocarbons Section 20.1 Steven S. Zumdahl Susan A. Zumdahl Donald J. DeCoste Gretchen M. Adams University of Illinois at Urbana-Champaign Chapter.](https://reader036.fdocuments.in/reader036/viewer/2022062301/56649e4d5503460f94b42c16/html5/thumbnails/36.jpg)
Section 20.3
Introduction to Functional Groups and Alcohols
B. Alcohols
• All alcohols contain the –OH group.
![Page 37: Saturated Hydrocarbons Section 20.1 Steven S. Zumdahl Susan A. Zumdahl Donald J. DeCoste Gretchen M. Adams University of Illinois at Urbana-Champaign Chapter.](https://reader036.fdocuments.in/reader036/viewer/2022062301/56649e4d5503460f94b42c16/html5/thumbnails/37.jpg)
Section 20.3
Introduction to Functional Groups and Alcohols
B. Alcohols
![Page 38: Saturated Hydrocarbons Section 20.1 Steven S. Zumdahl Susan A. Zumdahl Donald J. DeCoste Gretchen M. Adams University of Illinois at Urbana-Champaign Chapter.](https://reader036.fdocuments.in/reader036/viewer/2022062301/56649e4d5503460f94b42c16/html5/thumbnails/38.jpg)
Section 20.3
Introduction to Functional Groups and Alcohols
The different kinds of alcohols
• Alcohols fall into different classes depending on where the –OH is positioned on the chain of carbon atoms.
• There are some chemical differences between the various types.
• Primary, Secondary, and Tertiary alcohols will be discussed on the next several slides.
• Common alcohols: – Methanol-wood alcohol– Ethanol-as an antiseptic and in alcoholic beverages– Isopropanol-in rubbing alcohol
![Page 39: Saturated Hydrocarbons Section 20.1 Steven S. Zumdahl Susan A. Zumdahl Donald J. DeCoste Gretchen M. Adams University of Illinois at Urbana-Champaign Chapter.](https://reader036.fdocuments.in/reader036/viewer/2022062301/56649e4d5503460f94b42c16/html5/thumbnails/39.jpg)
Section 20.3
Introduction to Functional Groups and Alcohols
Primary Alcohols
• In a primary (1o) alcohol, the carbon which carries the –OH group is only attached to one alkyl group.
• Examples of primary alcohols:
Ethanol 1-propanol 2-methyl-1-propanol
![Page 40: Saturated Hydrocarbons Section 20.1 Steven S. Zumdahl Susan A. Zumdahl Donald J. DeCoste Gretchen M. Adams University of Illinois at Urbana-Champaign Chapter.](https://reader036.fdocuments.in/reader036/viewer/2022062301/56649e4d5503460f94b42c16/html5/thumbnails/40.jpg)
Section 20.3
Introduction to Functional Groups and Alcohols
Secondary Alcohols
• In a secondary (2o) alcohol, the carbon with the –OH group attached is joined directly to two alkyl groups, which may be the same or different.
• Examples
2-propanol 2-butanol 3-pentanol
![Page 41: Saturated Hydrocarbons Section 20.1 Steven S. Zumdahl Susan A. Zumdahl Donald J. DeCoste Gretchen M. Adams University of Illinois at Urbana-Champaign Chapter.](https://reader036.fdocuments.in/reader036/viewer/2022062301/56649e4d5503460f94b42c16/html5/thumbnails/41.jpg)
Section 20.3
Introduction to Functional Groups and Alcohols
Tertiary Alcohols
• In a tertiary (3o) alcohol, the carbon with the –OH group attached is joined directly to three alkyl groups, which may be the same or different.
• Examples
2-methyl-2-propanol 2-methyl-2-butanol
![Page 42: Saturated Hydrocarbons Section 20.1 Steven S. Zumdahl Susan A. Zumdahl Donald J. DeCoste Gretchen M. Adams University of Illinois at Urbana-Champaign Chapter.](https://reader036.fdocuments.in/reader036/viewer/2022062301/56649e4d5503460f94b42c16/html5/thumbnails/42.jpg)
Section 20.3
Introduction to Functional Groups and Alcohols
C. Properties and Uses of Alcohols
• Methanol starting material for making acetic acid and many
adhesives, fibers and plastics motor fuel
• Ethanol Fermentation product
Fuel additive used to make gasohol
![Page 43: Saturated Hydrocarbons Section 20.1 Steven S. Zumdahl Susan A. Zumdahl Donald J. DeCoste Gretchen M. Adams University of Illinois at Urbana-Champaign Chapter.](https://reader036.fdocuments.in/reader036/viewer/2022062301/56649e4d5503460f94b42c16/html5/thumbnails/43.jpg)
Section 20.3
Introduction to Functional Groups and Alcohols
C. Properties and Uses of Alcohols
• Other alcohols Ethylene glycol (ethane-1,2-diol) – automotive antifreeze Phenol (benzenol) – production of adhesives and
plastics
![Page 44: Saturated Hydrocarbons Section 20.1 Steven S. Zumdahl Susan A. Zumdahl Donald J. DeCoste Gretchen M. Adams University of Illinois at Urbana-Champaign Chapter.](https://reader036.fdocuments.in/reader036/viewer/2022062301/56649e4d5503460f94b42c16/html5/thumbnails/44.jpg)
Section 20.3
Introduction to Functional Groups and Alcohols
C. Ethers
• An ether is a hydrocarbon with an oxygen sandwiched between the carbons.
• They tend to by very good solvents, much like water, and have relatively low reactivity.
![Page 45: Saturated Hydrocarbons Section 20.1 Steven S. Zumdahl Susan A. Zumdahl Donald J. DeCoste Gretchen M. Adams University of Illinois at Urbana-Champaign Chapter.](https://reader036.fdocuments.in/reader036/viewer/2022062301/56649e4d5503460f94b42c16/html5/thumbnails/45.jpg)
Section 20.3
Introduction to Functional Groups and Alcohols
Rules for Naming Ethers (common method)
• There are two predominate methods of naming ethers. The first is the common method and is most useful with simple ethers.
(The second method is preferred; next slide) • For the first method, if the carbon chains one side of the
oxygen are considered alkyl groups you simply name the groups then write ether.
CH3
CH2
O CH3
Ethyl methyl ether
![Page 46: Saturated Hydrocarbons Section 20.1 Steven S. Zumdahl Susan A. Zumdahl Donald J. DeCoste Gretchen M. Adams University of Illinois at Urbana-Champaign Chapter.](https://reader036.fdocuments.in/reader036/viewer/2022062301/56649e4d5503460f94b42c16/html5/thumbnails/46.jpg)
Section 20.3
Introduction to Functional Groups and Alcohols
Rules for Naming Ethers (Preferred method)
• The other method follows the official IUPAC rules: • Determine the longest alkyl chain for the root name. • Treat the oxygen and the remaining carbons as aside
chain. • The prefix includes the alkyl chain with a suffix of oxy for
the oxygen.
CH3
CH2
O CH3
methoxyethane
![Page 47: Saturated Hydrocarbons Section 20.1 Steven S. Zumdahl Susan A. Zumdahl Donald J. DeCoste Gretchen M. Adams University of Illinois at Urbana-Champaign Chapter.](https://reader036.fdocuments.in/reader036/viewer/2022062301/56649e4d5503460f94b42c16/html5/thumbnails/47.jpg)
Section 20.3
Introduction to Functional Groups and Alcohols
Practice Naming Ethers (answers next slide!)
![Page 48: Saturated Hydrocarbons Section 20.1 Steven S. Zumdahl Susan A. Zumdahl Donald J. DeCoste Gretchen M. Adams University of Illinois at Urbana-Champaign Chapter.](https://reader036.fdocuments.in/reader036/viewer/2022062301/56649e4d5503460f94b42c16/html5/thumbnails/48.jpg)
Section 20.3
Introduction to Functional Groups and Alcohols
Answers to Last Slide
(a) Diisopropyl ether
(a) Cyclopentyl propyl ether
(a) 4-Bromo-1-methoxybenzene
(d) 1-Methoxycyclohexene
(d) Ethyl isobutyl ether
![Page 49: Saturated Hydrocarbons Section 20.1 Steven S. Zumdahl Susan A. Zumdahl Donald J. DeCoste Gretchen M. Adams University of Illinois at Urbana-Champaign Chapter.](https://reader036.fdocuments.in/reader036/viewer/2022062301/56649e4d5503460f94b42c16/html5/thumbnails/49.jpg)
Section 20.3
Introduction to Functional Groups and Alcohols
Preparation of Ethers
• Dehydration of two alcohols:
• Alkyl halide and alkoxide:
![Page 50: Saturated Hydrocarbons Section 20.1 Steven S. Zumdahl Susan A. Zumdahl Donald J. DeCoste Gretchen M. Adams University of Illinois at Urbana-Champaign Chapter.](https://reader036.fdocuments.in/reader036/viewer/2022062301/56649e4d5503460f94b42c16/html5/thumbnails/50.jpg)
Section 20.4
Additional Organic Compounds
1. To learn about aldehydes and ketones
2. To learn to name aldehydes and ketones
3. To learn about some common carboxylic acids and esters
4. To learn about amines.
5. To learn how to name amines.
6. To learn about some common polymers
Objectives
![Page 51: Saturated Hydrocarbons Section 20.1 Steven S. Zumdahl Susan A. Zumdahl Donald J. DeCoste Gretchen M. Adams University of Illinois at Urbana-Champaign Chapter.](https://reader036.fdocuments.in/reader036/viewer/2022062301/56649e4d5503460f94b42c16/html5/thumbnails/51.jpg)
Section 20.4
Additional Organic Compounds
A. Aldehydes and Ketones
• Carbonyl group – carbon oxygen group found in both aldehydes and ketones
Ketone – carbonyl group is bonded to two carbon atoms
![Page 52: Saturated Hydrocarbons Section 20.1 Steven S. Zumdahl Susan A. Zumdahl Donald J. DeCoste Gretchen M. Adams University of Illinois at Urbana-Champaign Chapter.](https://reader036.fdocuments.in/reader036/viewer/2022062301/56649e4d5503460f94b42c16/html5/thumbnails/52.jpg)
Section 20.4
Additional Organic Compounds
A. Aldehydes and Ketones
Aldehyde – carbonyl group always appears on the end of the hydrocarbon chain and has at least one H atom bonded to the carbonyl group
![Page 53: Saturated Hydrocarbons Section 20.1 Steven S. Zumdahl Susan A. Zumdahl Donald J. DeCoste Gretchen M. Adams University of Illinois at Urbana-Champaign Chapter.](https://reader036.fdocuments.in/reader036/viewer/2022062301/56649e4d5503460f94b42c16/html5/thumbnails/53.jpg)
Section 20.4
Additional Organic Compounds
A. Aldehydes and Ketones
![Page 54: Saturated Hydrocarbons Section 20.1 Steven S. Zumdahl Susan A. Zumdahl Donald J. DeCoste Gretchen M. Adams University of Illinois at Urbana-Champaign Chapter.](https://reader036.fdocuments.in/reader036/viewer/2022062301/56649e4d5503460f94b42c16/html5/thumbnails/54.jpg)
Section 20.4
Additional Organic Compounds
B. Naming Aldehydes and Ketones
• Aldehydes
Use the parent alkane name. • Remove the e and replace it with al.
![Page 55: Saturated Hydrocarbons Section 20.1 Steven S. Zumdahl Susan A. Zumdahl Donald J. DeCoste Gretchen M. Adams University of Illinois at Urbana-Champaign Chapter.](https://reader036.fdocuments.in/reader036/viewer/2022062301/56649e4d5503460f94b42c16/html5/thumbnails/55.jpg)
Section 20.4
Additional Organic Compounds
B. Naming Aldehydes and Ketones
• Ketones
Use the parent alkane name. • Remove the e and replace it with one. • Use a number to indicate the position of the
carbonyl group in the hydrocarbon chain. Select the number so that the carbonyl has the lowest
possible number.
Propanone (acetone)2-butanone (methyl-ethyl-ketone MEK)
![Page 56: Saturated Hydrocarbons Section 20.1 Steven S. Zumdahl Susan A. Zumdahl Donald J. DeCoste Gretchen M. Adams University of Illinois at Urbana-Champaign Chapter.](https://reader036.fdocuments.in/reader036/viewer/2022062301/56649e4d5503460f94b42c16/html5/thumbnails/56.jpg)
Section 20.4
Additional Organic Compounds
C. Carboxylic Acids and Esters
• Carboxylic acids – contains the carboxyl group
COOH
• General formula RCOOH • Weak acids in solution
![Page 57: Saturated Hydrocarbons Section 20.1 Steven S. Zumdahl Susan A. Zumdahl Donald J. DeCoste Gretchen M. Adams University of Illinois at Urbana-Champaign Chapter.](https://reader036.fdocuments.in/reader036/viewer/2022062301/56649e4d5503460f94b42c16/html5/thumbnails/57.jpg)
Section 20.4
Additional Organic Compounds
C. Carboxylic Acids and Esters
• To name carboxylic acids
Use the parent alkane name. • Remove the e and replace it with oic.
![Page 58: Saturated Hydrocarbons Section 20.1 Steven S. Zumdahl Susan A. Zumdahl Donald J. DeCoste Gretchen M. Adams University of Illinois at Urbana-Champaign Chapter.](https://reader036.fdocuments.in/reader036/viewer/2022062301/56649e4d5503460f94b42c16/html5/thumbnails/58.jpg)
Section 20.4
Additional Organic Compounds
C. Carboxylic Acids and Esters
![Page 59: Saturated Hydrocarbons Section 20.1 Steven S. Zumdahl Susan A. Zumdahl Donald J. DeCoste Gretchen M. Adams University of Illinois at Urbana-Champaign Chapter.](https://reader036.fdocuments.in/reader036/viewer/2022062301/56649e4d5503460f94b42c16/html5/thumbnails/59.jpg)
Section 20.4
Additional Organic Compounds
C. Carboxylic Acids and Esters
• Esters – a carboxylic acid reacts with an alcohol to form an ester and a water molecule
General formula
![Page 60: Saturated Hydrocarbons Section 20.1 Steven S. Zumdahl Susan A. Zumdahl Donald J. DeCoste Gretchen M. Adams University of Illinois at Urbana-Champaign Chapter.](https://reader036.fdocuments.in/reader036/viewer/2022062301/56649e4d5503460f94b42c16/html5/thumbnails/60.jpg)
Section 20.4
Additional Organic Compounds
C. Carboxylic Acids and Esters
• To name esters
Use the alkyl name from the alcohol followed by the acid name, where the –ic ending is replaced by –ate.
isopropylethanoate
![Page 61: Saturated Hydrocarbons Section 20.1 Steven S. Zumdahl Susan A. Zumdahl Donald J. DeCoste Gretchen M. Adams University of Illinois at Urbana-Champaign Chapter.](https://reader036.fdocuments.in/reader036/viewer/2022062301/56649e4d5503460f94b42c16/html5/thumbnails/61.jpg)
Section 20.4
Additional Organic Compounds
Amines
• What are amines?
• The easiest way to think of amines is as near relatives of ammonia, NH3.
• In amines, the hydrogen atoms in the ammonia have been replaced one at a time by hydrocarbon groups.
On this page, we are only looking at cases where the hydrocarbon groups are simple alkyl groups.
![Page 62: Saturated Hydrocarbons Section 20.1 Steven S. Zumdahl Susan A. Zumdahl Donald J. DeCoste Gretchen M. Adams University of Illinois at Urbana-Champaign Chapter.](https://reader036.fdocuments.in/reader036/viewer/2022062301/56649e4d5503460f94b42c16/html5/thumbnails/62.jpg)
Section 20.4
Additional Organic Compounds
The different kinds of amines
• Amines fall into different classes depending on how many of the hydrogen atoms are replaced.
Primary Secondary Tertiary
In a primary (1°) amine, one carbon group is bonded to the nitrogen atom.
A secondary (2°) amine has two carbon groups.
A tertiary (3°) amine has three carbon groups.
![Page 63: Saturated Hydrocarbons Section 20.1 Steven S. Zumdahl Susan A. Zumdahl Donald J. DeCoste Gretchen M. Adams University of Illinois at Urbana-Champaign Chapter.](https://reader036.fdocuments.in/reader036/viewer/2022062301/56649e4d5503460f94b42c16/html5/thumbnails/63.jpg)
Section 20.4
Additional Organic Compounds
Common Names of Amines
• Simple amines are named as alkylamines.• The alkyl groups bonded to the N atom are listed in
alphabetical order in front of amine.
![Page 64: Saturated Hydrocarbons Section 20.1 Steven S. Zumdahl Susan A. Zumdahl Donald J. DeCoste Gretchen M. Adams University of Illinois at Urbana-Champaign Chapter.](https://reader036.fdocuments.in/reader036/viewer/2022062301/56649e4d5503460f94b42c16/html5/thumbnails/64.jpg)
Section 20.4
Additional Organic Compounds
IUPAC Names of Amines
• In the IUPAC system, amines are named as alkanamines.
• The –e in the alkane name of the longest chain is changed to –amine.
• The chain is numbered to locate the amine group and substituents.
![Page 65: Saturated Hydrocarbons Section 20.1 Steven S. Zumdahl Susan A. Zumdahl Donald J. DeCoste Gretchen M. Adams University of Illinois at Urbana-Champaign Chapter.](https://reader036.fdocuments.in/reader036/viewer/2022062301/56649e4d5503460f94b42c16/html5/thumbnails/65.jpg)
Section 20.4
Additional Organic Compounds
Primary amines
• In primary amines, only one of the hydrogen atoms in the ammonia molecule has been replaced.
That means that the formula of the primary amine will be R-NH2 where "R" is an alkyl group.
• Examples include:
MethanamineEthanamine Propanamine Isopropanamine
![Page 66: Saturated Hydrocarbons Section 20.1 Steven S. Zumdahl Susan A. Zumdahl Donald J. DeCoste Gretchen M. Adams University of Illinois at Urbana-Champaign Chapter.](https://reader036.fdocuments.in/reader036/viewer/2022062301/56649e4d5503460f94b42c16/html5/thumbnails/66.jpg)
Section 20.4
Additional Organic Compounds
• The common name at this level is methylamine and, similarly, the second compound drawn above is usually called ethylamine.
• Where there might be confusion about where the -NH2 group is attached to a chain, the simplest way of naming the compound is to use the "amino" form.
![Page 67: Saturated Hydrocarbons Section 20.1 Steven S. Zumdahl Susan A. Zumdahl Donald J. DeCoste Gretchen M. Adams University of Illinois at Urbana-Champaign Chapter.](https://reader036.fdocuments.in/reader036/viewer/2022062301/56649e4d5503460f94b42c16/html5/thumbnails/67.jpg)
Section 20.4
Additional Organic Compounds
Secondary amines
• In a secondary amine, two of the hydrogens in an ammonia molecule have been replaced by hydrocarbon groups. At this level, you are only likely to come across simple ones where both of the hydrocarbon groups are alkyl groups and both are the same.
• Dimethanamine diethanamine
![Page 68: Saturated Hydrocarbons Section 20.1 Steven S. Zumdahl Susan A. Zumdahl Donald J. DeCoste Gretchen M. Adams University of Illinois at Urbana-Champaign Chapter.](https://reader036.fdocuments.in/reader036/viewer/2022062301/56649e4d5503460f94b42c16/html5/thumbnails/68.jpg)
Section 20.4
Additional Organic Compounds
Tertiary amines
• In a tertiary amine, all of the hydrogens in an ammonia molecule have been replaced by hydrocarbon groups. Again, you are only likely to come across simple ones where all three of the hydrocarbon groups are alkyl groups and all three are the same.
• The naming is similar to secondary amines. For example:
![Page 69: Saturated Hydrocarbons Section 20.1 Steven S. Zumdahl Susan A. Zumdahl Donald J. DeCoste Gretchen M. Adams University of Illinois at Urbana-Champaign Chapter.](https://reader036.fdocuments.in/reader036/viewer/2022062301/56649e4d5503460f94b42c16/html5/thumbnails/69.jpg)
Section 20.4
Additional Organic Compounds
Physical Properties of Amines
We will look at the boiling point difference on the next several slides.
![Page 70: Saturated Hydrocarbons Section 20.1 Steven S. Zumdahl Susan A. Zumdahl Donald J. DeCoste Gretchen M. Adams University of Illinois at Urbana-Champaign Chapter.](https://reader036.fdocuments.in/reader036/viewer/2022062301/56649e4d5503460f94b42c16/html5/thumbnails/70.jpg)
Section 20.4
Additional Organic Compounds
Primary amines
• It is useful to compare the boiling point of methylamine, CH3NH2, with that of ethane, CH3CH3.
• Both molecules contain the same number of electrons and have, as near as makes no difference, the same shape. However, the boiling point of methylamine is -6.3°C, whereas ethane's boiling point is much lower at -88.6°C.
• The reason for the higher boiling points of the primary amines is that they can form hydrogen bonds with each other as well as van der Waals dispersion forces and dipole-dipole interactions.
![Page 71: Saturated Hydrocarbons Section 20.1 Steven S. Zumdahl Susan A. Zumdahl Donald J. DeCoste Gretchen M. Adams University of Illinois at Urbana-Champaign Chapter.](https://reader036.fdocuments.in/reader036/viewer/2022062301/56649e4d5503460f94b42c16/html5/thumbnails/71.jpg)
Section 20.4
Additional Organic Compounds
Secondary amines
• For a fair comparison you would have to compare the boiling point of dimethylamine with that of ethylamine. They are isomers of each other - each contains exactly the same number of the same atoms.
• The boiling point of the secondary amine is a little lower than the corresponding primary amine with the same number of carbon atoms.
• Secondary amines still form hydrogen bonds, but having the nitrogen atom in the middle of the chain rather than at the end makes the permanent dipole on the molecule slightly less.
• The lower boiling point is due to the lower dipole-dipole attractions in the dimethylamine compared with ethylamine.
![Page 72: Saturated Hydrocarbons Section 20.1 Steven S. Zumdahl Susan A. Zumdahl Donald J. DeCoste Gretchen M. Adams University of Illinois at Urbana-Champaign Chapter.](https://reader036.fdocuments.in/reader036/viewer/2022062301/56649e4d5503460f94b42c16/html5/thumbnails/72.jpg)
Section 20.4
Additional Organic Compounds
Tertiary amines
• This time to make a fair comparison you would have to compare trimethylamine with its isomer 1-aminopropane.
• If you look back at the table on slide 18, you will see that the trimethylamine has a much lower boiling point (3.5°C) than 1-aminopropane (48.6°C).
• In a tertiary amine there aren't any hydrogen atoms attached directly to the nitrogen. That means that hydrogen bonding between tertiary amine molecules is impossible. That's why the boiling point is much lower.
![Page 73: Saturated Hydrocarbons Section 20.1 Steven S. Zumdahl Susan A. Zumdahl Donald J. DeCoste Gretchen M. Adams University of Illinois at Urbana-Champaign Chapter.](https://reader036.fdocuments.in/reader036/viewer/2022062301/56649e4d5503460f94b42c16/html5/thumbnails/73.jpg)
Section 20.4
Additional Organic Compounds
Solubility in water•The small amines of all types are very soluble in water. In fact, the ones that would normally be found as gases at room temperature are normally sold as solutions in water - in much the same way that ammonia is usually supplied as ammonia solution.
Smell•The very small amines like methylamine and ethylamine smell very similar to ammonia - although if you compared them side by side, the amine smells are slightly more complex.•As the amines get bigger, they tend to smell more "fishy", or they smell of decay.
![Page 74: Saturated Hydrocarbons Section 20.1 Steven S. Zumdahl Susan A. Zumdahl Donald J. DeCoste Gretchen M. Adams University of Illinois at Urbana-Champaign Chapter.](https://reader036.fdocuments.in/reader036/viewer/2022062301/56649e4d5503460f94b42c16/html5/thumbnails/74.jpg)
Section 20.4
Additional Organic Compounds
D. Polymers
• Polymers – large chainlike molecules made from many small molecules called monomers Simplest polymer – polyethylene Polyethylene results from addition polymerization.
![Page 75: Saturated Hydrocarbons Section 20.1 Steven S. Zumdahl Susan A. Zumdahl Donald J. DeCoste Gretchen M. Adams University of Illinois at Urbana-Champaign Chapter.](https://reader036.fdocuments.in/reader036/viewer/2022062301/56649e4d5503460f94b42c16/html5/thumbnails/75.jpg)
Section 20.4
Additional Organic Compounds
D. Polymers
• Condensation polymerization – a small molecule (often water) is released for each addition of a monomer to the polymer chain
• Copolymer – 2 different types of monomers combine to form the chain
Nylon (co-polymer)
![Page 76: Saturated Hydrocarbons Section 20.1 Steven S. Zumdahl Susan A. Zumdahl Donald J. DeCoste Gretchen M. Adams University of Illinois at Urbana-Champaign Chapter.](https://reader036.fdocuments.in/reader036/viewer/2022062301/56649e4d5503460f94b42c16/html5/thumbnails/76.jpg)
Section 20.4
Additional Organic Compounds
Sodium Silicate polymer
• When sodium silicate and ethyl alcohol are put together, the silicate particles begin to link up with each other to form long chains as the ethyl groups (sometimes shown as "R") replace oxygen atoms in the silicate ion. (Some become cross-linked between chains.) Water molecules are by-products of the formation of the polymerization bond.
• The large molecule is a solid. It is a type of silicone polymer.