1. Butane. 2. trans-2-methylcyclohexanol. 3. 1,2-dimethylcyclohexene. Chem 131 Spring 2018 Exam I Practice
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1 Chem 131 Spring 2018 Exam I Practice Thursday s examination will contain 31 questions valued at 3.5 points/question, with some bonus possibilities available Name KEY Name the following compounds. 1. Butane 2. trans-2-methylcyclohexanol 3. 1,2-dimethylcyclohexene 4. cis, trans-2,4-hexadiene
2 O 5. 2-hydroxybenzoic acid (or ortho-hydroxybenzoic acid) HO HO 6. 1,2,3-propanetriol (glycerol or glycerin) HO 7. 1,2,3-propanetriol (preferred to 1,2,3-trihydroxypropane) O 8. Diphenyl ether (or phenoxybenzene) SH 9. Cyclohexanethiol (or mercaptocyclohexane)
3 Please draw the structure of 10. cis-1,3-hexadiene Notice there is no cis/trans possibility at the 1 position methylcyclopentene: methyl-3-cyclopenten-1-ol: HO 13. mercaptoethane: SH 14. ortho-chlorobenzoic acid: O Cl 15. Phenyl methyl ether O
4 16. para-hydroxyaniline: N H 2 Bonus (1 EC each!): Provide as many alternative names as possible for para-hydroxyaniline para-aminophenol 4-hydroxyaniline 4-aminophenol 1-hydroxy-4-aminobenzene 17. Identify whether the bond-line formulas shown represent the same compound, cis-trans isomers, constitutional isomers, or compounds that are not isomers Answer: Constitutional isomers Cyclic molecules or those containing a double bond require 2 fewer hydrogen than a corresponding non-cyclic alkane 18. Identify whether the bond-line formulas shown represent the same compound, cis-trans isomers, constitutional isomers, or compounds that are not isomers Answer: Same compound rotate by 180 o in plane of paper
5 19. Which member in each of the following pairs of compounds has the higher boiling point? Hexane and 1-pentanol Pentane and 1-hexanol No contest between pentane and n-hexanol as n-hexanol is both bigger and hydrogen bonds. Hexane bp = 68 o C, n-pentanol bp = 137 o C. The power of hydrogen bonding 20. Which member in each of the following pairs of compounds has the greatest water solubility? 1-Hexanol and 1-pentanol 6:1 vs. 5:1 Phenol and cyclohexanol A bit tricky extra polarization due to benzene ring gives slight difference 21. Which of the following compounds would have the highest boiling point? a. b. c. d. Both large surface area and hydrogen bonding capacity - additive
6 22. Which of the following compounds would have the greatest water solubility? a. b. 6:1 C:O c. d. 10:1 C:O In questions 29 30, providing the name of the final compound will earn you 1 EC point 23. Please give the major product for the following reaction. If there is no + H2O H + Name: 2-butanol 24. Please give the major product for the following reaction. If there is no + HCl Name: 3-chloro-3-ethylpentane
7 25. Please give the major product for the following reaction. If there is no + H2O H + Name: 1-methylbenzyl alcohol or 1-hydroxy-1-phenylethane 26. Please give the major product for the following reaction. If there is no + Br2 Name: 1,2-dibromo-1-phenylethane 27. Please give the major product for the following reaction. If there is no + Cl2 FeCl3 Name: 2-chlorophenol or 4-chlorophenol The increased reactivity of the phenol compared to benzene would rapidly lead to 2,4,6-trichlorophenol. Do not expect a problem like this on the exam.
8 In keeping with the Reactions of Organic Compounds lab, note K2Cr2O7 in H2SO4 could be substituted as an oxidizing agent for KMnO4 in each of the following problems and yield the same product 28. Please give the major product for the following reaction. If there is no KMnO4 Name: No Reaction No H on the C bearing the oxygen 29. Please give the major product for the following reaction. If there is no KMnO4 Name: Benzoic acid (primary alcohol) Primary alcohols oxidize to carboxylic acids. Oxidation proceeds first to the aldehyde, and then on to the acid 30. Please give the major product for the following reaction. If there is no KMnO4 Name: Methyl phenyl ketone (secondary alcohol) 2 o alcohols can oxidize no further than ketone (C bearing oxygen runs out of H at this point). Tertiary alcohols resist oxidation altogether.
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