Organic Chemistry and Polymers

Copyright © Houghton Mifflin Company. All rights reserved. 22a–2 Computer model of a globular protein

Copyright © Houghton Mifflin Company. All rights reserved. 22a–3 Figure 22.1: C-H bonds in methane

Copyright © Houghton Mifflin Company. All rights reserved. 22a–4 Figure 22.2: (a) Lewis stucture of ethane (C2H6). (b) molecular structure of ethane

Copyright © Houghton Mifflin Company. All rights reserved. 22a–5 Figure 22.3: Structures of (a) propane (b) butane

Copyright © Houghton Mifflin Company. All rights reserved. 22a–6 Figure 22.4: (a) normal butane (b) branched isomer

Copyright © Houghton Mifflin Company. All rights reserved. 22a–7 Pentane

Copyright © Houghton Mifflin Company. All rights reserved. 22a–8 Isopentane

Copyright © Houghton Mifflin Company. All rights reserved. 22a–9 Neopentane

Copyright © Houghton Mifflin Company. All rights reserved. 22a–10

Copyright © Houghton Mifflin Company. All rights reserved. 22a–11 Figure 22.5: (a) molecular structure of cyclopropane (b) overlap of sp 3 orbitals

Copyright © Houghton Mifflin Company. All rights reserved. 22a–12 Figure 22.6: (a) chair (b) boat forms

Copyright © Houghton Mifflin Company. All rights reserved. 22a–13 Fractional Distillation

Copyright © Houghton Mifflin Company. All rights reserved. 22a–14 Petroleum Fractional Distillation

Copyright © Houghton Mifflin Company. All rights reserved. 22a–15 p.547a

Copyright © Houghton Mifflin Company. All rights reserved. 22a–16 Octane Number rating of gasoline’s ability to smoothly burn in an inertnal combustion engine

Copyright © Houghton Mifflin Company. All rights reserved. 22a–17 Combustion of Gasoline

Copyright © Houghton Mifflin Company. All rights reserved. Internal Combustion Engine C 9 H 20(l) + 14O 2(g)  9CO 2(g) + 10H 2 O (g) CH 3 CH 3 | | CH 3 - C - CH 2 - CH - CH 3 | CH 3 isooctane

Copyright © Houghton Mifflin Company. All rights reserved. 22a–19 Table 12-1, p.547

Copyright © Houghton Mifflin Company. All rights reserved. 22a–20 Octane Enhancers tetraethyl lead - (C 2 H 5 ) 4 Pb - antiknock additive to gasoline from , ~3g of lead per gallon of gasoline ethyl bromide was added to help precipitate lead from the air replaced by toluene, tert-butyl alcohol, methanol, ethanol, etc.

Copyright © Houghton Mifflin Company. All rights reserved. 22a–21 Figure 22.8: Bonding in ethane

Copyright © Houghton Mifflin Company. All rights reserved. 22a–22 Average Emissions per Vehicles

Copyright © Houghton Mifflin Company. All rights reserved. 22a–23 Natural Gas & Oil Production

Copyright © Houghton Mifflin Company. All rights reserved. Coal most coal is burned to produce electricity over 300 million tons of coal per year all coal contains some sulfur burning coal produces SO 2 and SO 3

Copyright © Houghton Mifflin Company. All rights reserved. 22a–25 Figure 22.7: Bonding in ethylene

Copyright © Houghton Mifflin Company. All rights reserved. 22a–26 Figure 22.9: The two stereoisomers of 2-butene

Copyright © Houghton Mifflin Company. All rights reserved. 22a–27 Figure 22.10: Bonding in acetylene

Copyright © Houghton Mifflin Company. All rights reserved. 22a–28 p.548

Copyright © Houghton Mifflin Company. All rights reserved. 22a–29 Fig. 12-3, p.548

Copyright © Houghton Mifflin Company. All rights reserved. 22a–30 Figure 22.11: The structure of benzene

Copyright © Houghton Mifflin Company. All rights reserved. 22a–31 Figure 22.12: Some selected substituted benzenes and their names

Copyright © Houghton Mifflin Company. All rights reserved. 22a–32

Copyright © Houghton Mifflin Company. All rights reserved. 22a–33 Compounds containing aromatic rings are often used in dyes, such as these for sale in a market in Nepal Source: Getty Images

Copyright © Houghton Mifflin Company. All rights reserved. 22a–34

Copyright © Houghton Mifflin Company. All rights reserved. 22a–35

Copyright © Houghton Mifflin Company. All rights reserved. 22a–36 Average Emissions per Vehicles

Copyright © Houghton Mifflin Company. All rights reserved. 22a–37 Natural Gas & Oil Production

Copyright © Houghton Mifflin Company. All rights reserved. Coal most coal is burned to produce electricity over 300 million tons of coal per year all coal contains some sulfur burning coal produces SO 2 and SO 3

Copyright © Houghton Mifflin Company. All rights reserved. 22a–39 Blood Alcohol Level

Copyright © Houghton Mifflin Company. All rights reserved. 22a–40 Alcohols and Water alcohols are “monosubstituted” water, ROH, hydrocarbon radical, R, substituted for one of the hydrogen atoms in water, HOH alcohols form hydrogen bonds to other alcohol molecules, increasing boiling point, and to water, making them very soluble in water

Copyright © Houghton Mifflin Company. All rights reserved. 22a–41 Classes of Alcohols

Copyright © Houghton Mifflin Company. All rights reserved. 22a–42 Oxidation of Alcohols primary alcohol  aldehyde  carboxylic acids RCH 2 OH  RCHO  RCOOH secondary alcohols  ketones RCHOHR’  RC=OR’ tertiary alcohols  No Reaction

Copyright © Houghton Mifflin Company. All rights reserved. 22a–43 Large Molecules Containing Alcohol Groups

Copyright © Houghton Mifflin Company. All rights reserved. 22a–44 More Large Molecules Containing Alcohol Groups

Copyright © Houghton Mifflin Company. All rights reserved. 22a–45 Ethanol is being tested in selected areas as a fuel for automobiles Source: AP/Wide World Photos

Copyright © Houghton Mifflin Company. All rights reserved. 22a–46 Cinnamaldehyde produces the characteristic odor of cinnamon Source: Visuals Unlimited

Copyright © Houghton Mifflin Company. All rights reserved. 22a–47 Figure 22.13: Some common ketones and akdehydes

Copyright © Houghton Mifflin Company. All rights reserved. 22a–48 Figure 22.14: Some carboxylic acids

Copyright © Houghton Mifflin Company. All rights reserved. 22a–49 Computer-generated space-filling model of acetylsalicylic acid (aspirin) Source: Photo Researchers, Inc.

Copyright © Houghton Mifflin Company. All rights reserved. 22a–50