Introduction to General, Organic and Biochemistry
11th Edition
ISBN: 9781285869759
Author: Frederick A. Bettelheim, William H. Brown, Mary K. Campbell, Shawn O. Farrell, Omar Torres
Publisher: Cengage Learning
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Chapter 14, Problem 14.70P
14-70 Show how to prepare each compound from 2-methylcyclohexanol.
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me
CH3
H3C
3-butylpropanoate
2-butoxypropane
propyl-2-butanoate
2-butylpropanoate
H₂
C
CH3
Name the following compound.
What is the reduction product of the following compound with H2/Pd?
A 2-propyl-1-cyclohexanol
B 2-propenyl-1-cyclohexanol
C2-propylcyclohexanone
D 1-propyl-2-cyclohexanol
What is the oxidation product of this compound?
H'
A ethanoic acid
acetic acid
propanoic acid
D propanone
What is the oxidation product of this compound?
A 3,4-dimethylpentanoic acid
B 2,3-dimethylpentanoic acid
C2,3-dimethylpentanone
3,4-dimethylpentanone
Chapter 14 Solutions
Introduction to General, Organic and Biochemistry
Ch. 14.1 - Prob. 14.1PCh. 14.1 - Prob. 14.2PCh. 14.2 - Problem 14-3 Draw structural formulas for the...Ch. 14.2 - Prob. 14.4PCh. 14.2 - Prob. 14.5PCh. 14.3 - Problem 14-6 Write the common name for each ether.Ch. 14.4 - Prob. 14.7PCh. 14 - 14-8 Answer true or false. The functional group of...Ch. 14 - 14-9 What is the difference in structure between a...Ch. 14 - 14-10 Which of the following are secondary...
Ch. 14 - 14-11 Which of the alcohols in Problem 14-10 are...Ch. 14 - 14-12 Write the 1UPAC name of each compound. (e)...Ch. 14 - Prob. 14.13PCh. 14 - Prob. 14.14PCh. 14 - 14-15 Both alcohols and phenols contain an —OH...Ch. 14 - Prob. 14.16PCh. 14 - 14-17 Explain in terms of noncovalent interactions...Ch. 14 - Prob. 14.18PCh. 14 - Prob. 14.19PCh. 14 - 14-20 Show hydrogen bonding between methanol and...Ch. 14 - 14-21 Show hydrogen bonding between the oxygen of...Ch. 14 - 14-22 Arrange these compounds in order of...Ch. 14 - 14-23 Arrange these compounds in order of...Ch. 14 - 14-24 2-Propanol (isopropyl alcohol) is commonly...Ch. 14 - 14-25 Explain why glycerol is much thicker (more...Ch. 14 - Prob. 14.26PCh. 14 - Prob. 14.27PCh. 14 - 14-28 Give the structural formula of an alkene or...Ch. 14 - Prob. 14.29PCh. 14 - 14-30 Show how to distinguish between cyclohexanol...Ch. 14 - 14-31 Compare the acidity of alcohols and phenols,...Ch. 14 - 14-32 Both 2,6-diisopropylcyclohexanol and the...Ch. 14 - 14-33 Write equations for the reaction of...Ch. 14 - 14-34 Write equations for the reaction of...Ch. 14 - 14-35 Write equations for the reaction of each of...Ch. 14 - 14-36 Show how to convert cyclohexanol to these...Ch. 14 - Prob. 14.37PCh. 14 - Prob. 14.38PCh. 14 - 14-39 Name two important alcohols derived from...Ch. 14 - 14-40 Name two important alcohols derived from...Ch. 14 - Prob. 14.41PCh. 14 - 14-42 Write the common name for each ether. ch3...Ch. 14 - Prob. 14.43PCh. 14 - 14-44 Answer true or false. (a) The functional...Ch. 14 - Prob. 14.45PCh. 14 - Prob. 14.46PCh. 14 - 14-47 Following are structural formulas for...Ch. 14 - 14-48 Explain why methanethiol, CH3SH, has a lower...Ch. 14 - 14-49 Answer true or false. Today, the major...Ch. 14 - Prob. 14.50PCh. 14 - 14-51 (Chemical Connections 14B) When was...Ch. 14 - 14-52 (Chemical Connections 14B) What was Alfred...Ch. 14 - Prob. 14.53PCh. 14 - 14-54 (Chemical Connections 14C) What is the color...Ch. 14 - 14-55 (Chemical Connections 140 The legal...Ch. 14 - 14-56 (Chemical Connections 14D) What does it mean...Ch. 14 - 14-57 (Chemical Connections 14E) What are the...Ch. 14 - Prob. 14.58PCh. 14 - Prob. 14.59PCh. 14 - 14-60 Write a balanced equation for the complete...Ch. 14 - 14-61 Knowing what you do about electronegativity,...Ch. 14 - 14-62 Draw structural formulas and write IUPAC...Ch. 14 - Prob. 14.63PCh. 14 - 14-64 Explain why the boiling point of ethylene...Ch. 14 - Prob. 14.65PCh. 14 - 14-66 1,4-Butanediol, hexane, and 1-pentanol have...Ch. 14 - 14-67 Of the three compounds given in Problem...Ch. 14 - Prob. 14.68PCh. 14 - 14-69 Show how to prepare each compound from...Ch. 14 - 14-70 Show how to prepare each compound from...Ch. 14 - 14-71 The mechanism of the acid-catalyzed...Ch. 14 - Prob. 14.72PCh. 14 - 14-73 Lipoic acid is a growth factor for many...Ch. 14 - 14-74 Following is a structural formula for the...Ch. 14 - Prob. 14.75PCh. 14 - Prob. 14.76PCh. 14 - Prob. 14.77PCh. 14 - 14-78 Consider alkenes A, B, and C. each of which...Ch. 14 - Prob. 14.79P
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- 14-69 Show how to prepare each compound from 2-methyl-1 -propanol. 2-Methylpropene 2-Methyl-2-propanol 2-Methylpropanoic acid, (CH3)2CHCOOHarrow_forward14-36 Show how to convert cyclohexanol to these compounds. Cyclohexene Cyclohexane Cyclohexanone Bromocyclohexanearrow_forward14-21 Show hydrogen bonding between the oxygen of di ethyl ether and a hydrogen of water.arrow_forward
- 14-34 Write equations for the reaction of 2-butanol with these reagents. H2SO4, heat K2Cr2O7, H2SO4arrow_forward14-57 (Chemical Connections 14E) What are the advantages and disadvantages of using diethyl ether as an anesthetic?arrow_forward17-79 Write an equation for each conversion. (a) 1-Pentanol to pentanal (b) 1-Pentanol to pentanoic acid (c) 2-Pentanol to 2-pentanone (d) 2-Propanol to acetone (e) Cyclohexanol to cyclohexanonearrow_forward
- 14-20 Show hydrogen bonding between methanol and water in the following ways. Between the oxygen of methanol and a hydrogen of water Between the hydrogen of methanol’s OH group and the oxygen of waterarrow_forward14-48 Explain why methanethiol, CH3SH, has a lower boiling point (6°C) than methanol, CH3OH (65°C), even though methanethiol has a higher molecular weightarrow_forward14-71 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: Break a bond to form stable molecules or ions. 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 bond-making or bond-breaking step occurs. H I + Step 3: CH3—CH—CH—CH3 CH3—CH=CH—CH3 + H + 2-butenearrow_forward
- 17-70 What simple chemical test could you use to distinguish between the members of each pair of com pounds? Tell what you would do, what you would expect to observe, and how you would interpret your experimental observation. (a) Benzaldehyde and cyclohexanone (b) Acetaldehyde and acetonearrow_forward17-3 1 Draw a structural formula for the principal organic product formed when each compound is treated with K2Cr2O7/H2SO4. If there is no reaction, say so. (a) Butanal (b) Benzaldehyde (c) Cyclohexanone (d) Cyclohexanolarrow_forward14-33 Write equations for the reaction of 1-butanol, a primary alcohol, with these reagents. H2SO4, heat K2Cr2O7, H2SO4arrow_forward
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