2. Which of the alcohols in Problem 1. Are primary? Which are tertiary? 4. Draw a structural formula for each of the following alcohols.

Size: px

Start display at page:

Download "2. Which of the alcohols in Problem 1. Are primary? Which are tertiary? 4. Draw a structural formula for each of the following alcohols."

Gregory Dean
7 years ago
Views:

1 CEM 122: Introduction to rganic Chemistry Chapter 5: Alcohols, Ethers, and Thiols. 1. Which of the following are secondary alcohols? C 3 b) (C3)3C c) 2. Which of the alcohols in Problem 1. Are primary? Which are tertiary? 3. Write the IUPAC name of each compound. b) c) e) f) 4. Draw a structural formula for each of the following alcohols. Isobutyl alcohol b) 1,4-Butanediol c) 5-Methyl-1-hexanol 1,3-Pentanediol e) trans-1,4-cyclohexanediol f) 3,3-Dimethylcyclohexanol 5. Both alcohols and phenols contain an group. What structural feature distinguishes these two classes of compounds? Illustrate your answer by drawing the structural formulas of a phenol with six carbon atoms and an alcohol with six carbon atoms. 6. Explain in terms of noncovalent interactions (intermolecular forces) why the lowmolecular-weight alcohols are more soluble in water than the low-molecularweight ethers. 7. Show hydrogen bonding between the oxyge3n of diethyl ether and a hydrogen of water.

2 8. Arrange these compounds in order of increasing boiling point. Values in o C are -42, 78, 117, and 198. C3C2C2C2 b) C3C2 c) C2C2 C3C2C3 9. From each pair, select the compound that is more soluble in water. C3 or C3C3 C2 b) C 3 CC 3 or C 3 CC 3 c) C 3 C 2 C 2 S or C 3 C 2 C Give the structural formula of an alkene or alkenes from which each alcohol can be prepared. 2-Butanol b) 1-Methylcyclohexanol c) 3-exanol 2-Methyl-2-pentanol e) Cyclopentanol 11. Both 2,6-diisopropylcyclohexanol and the intravenous anesthetic Propofol are insoluble in water. Show how these two compounds can be distinguished by their reaction with aqueous sodium hydroxide. 2,6-Diisopropylcyclohexanol 2,6-Diisopropylphenol (Propofol) 12. Write equations for the reaction of 2-butanol with these reagents. 2S4, heat b) K2Cr27, 2S4

3 13. Show how to convert cyclohexanol to these compounds. Cyclohexene b) Cyclohexane c) Cyclohexanone omocyclohexane 14. Show reagents and experimental conditions to synthesize each compound from 1- propanol. (e) ( (f) (b) (c) ( (g) (h) (i) 15. Write the common name for each ether. b) [C3(C2)4]2 c) C3CCC3 16. Write the IUPAC name of each thiol. S C3C2CC3 b) C3C2C2C2S c) 17. Write the common name for each thiol in Problem 16.

4 18. Explain why methanethiol, C3S, has a lower boiling point (6 o C) than methanol, C3 (65 o C), even though methanethiol has a higher molecular weight. 19. Draw structural formulas and write IUPAC names for the eight isomeric alcohols with the molecular formula C Draw structural formulas and write common names for the six isomeric ethers with the molecular formula C ,4-Butanediol, hexane, and 1-pentanol have similar molecular weights. Their boiling points, arranged from lowest to highest, are 69 o C, 138 o C, and 230 o C. Which compound has which boiling point? 22. f the three compounds given in Problem 21., one in insoluble in water, another has a solubility of 2.3 g/100g water, and one is infinitely soluble in water. Which compound has which solubility? 23. Show how to prepare each compound from 2-methylcyclohexanol. C 3 b) C 3 c) C 3 C 3

5 24. The mechanism of the acid-catalyzed dehydration of an alcohol to an alkene is the reverse of the acid-catalyzed hydration of an alkene. The dehydration mechanism occurs by the following three steps: Step 1: Add a proton. Step 2: eak a bond to form stable molecules or ion. Step 3: Take away a proton. These three steps are illustrated here by the dehydration of 2-butanol to give 2-butene. Use curved arrows to show the flow of electrons in each step; that is, show how each bondmaking or bond-breaking step occurs. Step 1: + Step 2: + 2 Step 3: and Use the reactions we learned in Chapter 3 and this chapter to show how to bring about the following chemical transformations. Some transformations will require only one step. thers will require two or more steps. b) c) C 2 e) C 3 f)

MULTIPLE CHOICE. Choose the one alternative that best completes the statement or answers the question.

Ch14_PT MULTIPLE CHOICE. Choose the one alternative that best completes the statement or answers the question. 1) Compounds with the -OH group attached to a saturated alkane-like carbon are known as A)