solut22 - CHAPTER TWENTY-TWO ORGANIC CHEMISTRY Hydrocarbons...

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590 CHAPTER TWENTY-TWO ORGANIC CHEMISTRY Hydrocarbons 1. A difficult task in this problem is recognizing different compounds from compounds that differ by rotations about one or more C-C bonds (called conformations). The best way to distinguish different compounds from conformations is to name them. Different name = different compound; same name = same compound so it is not an isomer, but instead, is a conformation. a. b.
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591
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CHAPTER 22 ORGANIC CHEMISTRY 592 c. d. 2. There is only one consecutive chain of C-atoms in the molecule. They are not all in a true straight line since the bond angles at each carbon atom are the tetrahedral angles of 109.5 ° . 3. a. b. CH 3 CC H 2 3 3 3 3 3 2 2 3 3
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CHAPTER 22 ORGANIC CHEMISTRY 593 c. d. The longest chain is 6 carbons long. 2,2,3-trimethylhexane 4. 5. a. 2,2,4-trimethylhexane b. 5-methylnonane c. 2,2,4,4-tetramethylpentane d. 3-ethyl-3-methyloctane Note: For alkanes always identify the longest carbon chain for the base name first, then number the carbons to give the lowest overall numbers for the substituent groups. 6. The hydrogen atoms in ring compounds are commonly omitted. In organic compounds, carbon atoms satisfy the octet rule of electrons by forming four bonds to other atoms. Therefore, add C-H bonds to the carbon atoms in the ring in order to give each C atom four bonds. You can also determine the formula of these cycloalkanes by using the general formula C n H 2n . a. ethylcyclobutane: C 6 H 12 b. 1-ethyl-3-isopropylcyclopentane; C 10 H 20 c. 2-ethyl-1,4-dimethylcyclohexane; C 10 H 20 Note: For compound b, 3-ethyl-1-isopropylcyclopentane has the same lowest numbers for the CH 3 2 2 3 CC H 3 3 3 1 2 34 6 5 3 2 2 3 H 3 3 3
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CHAPTER 22 ORGANIC CHEMISTRY 594 substituent groups as 1-ethyl-3-isopropylcyclopentane. When two different numbering systems each give the same lowest numbers, then number the carbons so the first substituent named has the lowest number. Hence, 1-ethyl-3-isopropylcyclopentane is preferred. 7. a. 1-butene b. 2-methyl-2-butene c. 2,5-dimethyl-3-heptene d. 2,3-dimethyl-1-pentene e. 1-ethyl-3-methylcyclopentene (double bond assumed between C 1 and C 2 ) f. 4-ethyl-3-methylcyclopentene g. 4-methyl-2-pentyne Note: Multiple bonds are assigned the lowest number possible.
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CHAPTER 22 ORGANIC CHEMISTRY 595 CH 3 CH 2 3 CC H 3 3 3 C H 3 C 3 3 CH 2 CH 3 CH 2 CH 3 2 3 8. a. CH 3 -CH 2 -CH_CH-CH 2 -CH 3 b. CH 3 -CH_CH-CH_CH-CH 2 CH 3 c. d. 9. a. 1,3-dichlorobutane b. 1,1,1-trichlorobutane c. 2,3-dichloro-2,4-dimethylhexane d. 1,2-difluoroethane e. 3-iodo-1-butene f. 2-bromotoluene (or 1-bromo-2-methylbenzene) g. 1-bromo-2-methylcyclohexane h. 4-bromo-3-methylcyclohexene (double bond assumed between C 1 and C 2 ) 10. a. b. c. d. 11. isopropylbenzene or 2-phenylpropane Isomerism 12. resonance: All atoms are in the same position. Only the position of π electrons are different.
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This homework help was uploaded on 04/06/2008 for the course CHEM 142 taught by Professor Zoller,williamh during the Fall '07 term at University of Washington.

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solut22 - CHAPTER TWENTY-TWO ORGANIC CHEMISTRY Hydrocarbons...

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