EBK ORGANIC CHEMISTRY
8th Edition
ISBN: 8220102744127
Author: Bruice
Publisher: PEARSON
expand_more
expand_more
format_list_bulleted
Concept explainers
Videos
Textbook Question
Chapter 10.4, Problem 19P
What stereoisomers are formed in the following reactions? Which stereoisomer is the major product?
- a. the acid-catalyzed dehydration of 1-pentanol to 2-pentene
- b. the acid-catalyzed dehydration of 3,4-dimethyl-3-hexanol to 3,4-dimethyl-3-hexene
Expert Solution & Answer
Want to see the full answer?
Check out a sample textbook solution
Students have asked these similar questions
What substitution products are obtained when each of the following compounds is added to a solution of sodium acetate in acetic acid?
a. 2-chloro-2-methyl-3-hexene
b. 3-bromo-1-methylcyclohexene
Consider the structure of pent-2-ene, if it undergoes ozonolysis, which of the following final product is formed?
a.Ethanal and Propanal
b.Ethanal and Propanone
c.CO2 and Propanal
d.Ethanal and CO2
Show how to convert cyclohexanol to these compounds.
a. Cyclohexene
b. Cyclohexane
c. Cyclohexanone
d. Bromocyclohexane
Chapter 10 Solutions
EBK ORGANIC CHEMISTRY
Ch. 10.1 - Why are NH3 and CH3NH2 no longer nucleophiles when...Ch. 10.1 - Explain the difference in reactivity between...Ch. 10.1 - Prob. 5PCh. 10.1 - Prob. 6PCh. 10.1 - Prob. 8PCh. 10.2 - Prob. 9PCh. 10.3 - Prob. 11PCh. 10.3 - Show how 1-propanol can be converted into the...Ch. 10.4 - Which of the following alcohols dehydrates the...Ch. 10.4 - Prob. 14P
Ch. 10.4 - Prob. 15PCh. 10.4 - Propose a mechanism for each of the following...Ch. 10.4 - Draw the product of each of the following...Ch. 10.4 - Explain why the following alcohols, when heated...Ch. 10.4 - What stereoisomers are formed in the following...Ch. 10.4 - Prob. 20PCh. 10.4 - What alcohol would you treat with phosphorus...Ch. 10.5 - Prob. 22PCh. 10.6 - What are the major products obtained when each of...Ch. 10.6 - Prob. 26PCh. 10.7 - Prob. 27PCh. 10.7 - Would you expect the reactivity of a five-membered...Ch. 10.7 - Prob. 29PCh. 10.7 - What products are obtained from the reaction of...Ch. 10.7 - Prob. 31PCh. 10.7 - Prob. 32PCh. 10.7 - Prob. 33PCh. 10.8 - Draw the mechanism for formation of the two...Ch. 10.8 - Prob. 35PCh. 10.8 - Prob. 36PCh. 10.8 - How do the major products obtained from...Ch. 10.8 - Explain why the two arene oxides in Problem 38...Ch. 10.8 - Which compound is more likely to be carcinogenic?Ch. 10.8 - Three arene oxides can be obtained from...Ch. 10.9 - Explain why the half-life (the time it takes for...Ch. 10.10 - Prob. 43PCh. 10.10 - Prob. 44PCh. 10.10 - Prob. 45PCh. 10.10 - Prob. 46PCh. 10.10 - Prob. 47PCh. 10.10 - Describe a synthesis for each of the following...Ch. 10.11 - Using an alkyl halide and a thiol as starting...Ch. 10.11 - The following three nitrogen mustards were studied...Ch. 10.11 - Why is melphalan a good cancer drug?Ch. 10.11 - Prob. 53PCh. 10.12 - Propose a mechanism for the following reaction:Ch. 10 - Prob. 55PCh. 10 - Which compound is more likely to be carcinogenic?Ch. 10 - Prob. 57PCh. 10 - Prob. 58PCh. 10 - When heated with H2SO4, both...Ch. 10 - What is the major product obtained from the...Ch. 10 - Write the appropriate reagent over each arrow.Ch. 10 - What alkenes would you expect to be obtained from...Ch. 10 - Prob. 63PCh. 10 - Prob. 64PCh. 10 - When deuterated phenanthrene oxide undergoes a...Ch. 10 - An unknown alcohol with a molecular formula of...Ch. 10 - Explain why the acid-catalyzed dehydration of an...Ch. 10 - Prob. 68PCh. 10 - Prob. 69PCh. 10 - Propose a mechanism for the following reaction:Ch. 10 - What product would be formed if the four-membered...Ch. 10 - Which of the following ethers would be obtained in...Ch. 10 - Using the given starting material any necessary...Ch. 10 - Prob. 74PCh. 10 - When 3-methyl-2-butanol is heated with...Ch. 10 - Draw structures for compounds AF.Ch. 10 - Propose a mechanism for each of the following...Ch. 10 - How could you synthesize isopropyl propyl ether,...Ch. 10 - When ethyl ether is heated with excess HI for...Ch. 10 - When the following seven-membered ring alcohol is...Ch. 10 - Ethylene oxide reacts readily with HO because of...Ch. 10 - Describe how each of the following compounds could...Ch. 10 - Propose a mechanism for each of the following...Ch. 10 - Triethylene glycol is one of the products obtained...Ch. 10 - Prob. 85PCh. 10 - Propose a mechanism for the following reaction:Ch. 10 - Prob. 87PCh. 10 - An ion with a positively charged nitrogen atom in...Ch. 10 - The following reaction takes place several times...Ch. 10 - Prob. 90PCh. 10 - Propose a mechanism for each of the following...Ch. 10 - A vicinal diol has OH groups on adjacent carbons....Ch. 10 - Prob. 93PCh. 10 - Prob. 94PCh. 10 - Two stereoisomers are obtained from the reaction...Ch. 10 - Propose a mechanism for each or the following...Ch. 10 - Triethylenemelamine (TEM) is an antitumor agent....
Knowledge Booster
Learn more about
Need a deep-dive on the concept behind this application? Look no further. Learn more about this topic, chemistry and related others by exploring similar questions and additional content below.Similar questions
- Which alcohols can be prepared as a single product by hydroboration– oxidation of an alkene? Which alcohols can be prepared as a single product by the acid-catalyzed addition of H2O to an alkene?arrow_forward. Which of the following can be both formed from bromoethane and converted directly into ethanal? CH3CH2Br → X → CH3CHO a. CH3CH2OH b. CH3OCH3 c. CH3COOH d. H2C=CHBrarrow_forward7) You want to synthesize 3-methyl-2-pentene from 2-chloro-3-methylpentane. Which reagent would you use? a. HCI, heat b. NH:(aq), 25°C c. CH:CO2NA, CH:CO2H, heat d. CH3CH2ONA, CH3CH2OH, heat e. CН:CH2ОН, heatarrow_forward
- What process will not yield carboxylic acid?arrow_forward40. Deuterium oxide, D20, is water that contains the stable hydrogen isotope 2H, usually shown as D. When dissolved in deuterium oxide, ethanol undergoes the following reaction: * CH3CH2OH + D½0 → CH;CH2OD + HOD What is the best way of showing that this reaction has occurred? A. By testing the product with phosphorus pentachloride and not getting steamy fumes. B. By determining the mass spectrum of the mixture and showing peaks at m/z values of 20 and 46. C. By fractionally distilling the mixture and determining the amount of CH3CH2OD using a Geiger counter. D. By determining the mass spectrum of the mixture and showing peaks at m/z values by 19 and 47. A В O Darrow_forwardWhat product(s) will form: 2-Pentene + H₂O → O a. 2-Pentanol O b. Isopropyl alcohol O c. 3-Pentanol O d. a 50/50 mixture of 2-Pentanol and 3-Pentanol Oe. no reaction will occurarrow_forward
- Determine the product of the reaction considering the conditions given. A. No product will be formed B. 2-methoxy-2,3,3-trimethylpentane C. 2,3,3-trimethyl-1-pentanearrow_forwardWhat is the major organic product obtained from the following reaction? A. 3-hydroxypropanoic acid B. 3-oxopropanoic acid C. propanedioic acid D. 1,3-propanediolarrow_forwardWhat explains why many aldehydes and ketones can undergo self- condensation reactions in basic conditions? A. The alpha carbon can lose a proton and act like a nucleophile and the carbonyl carbon a an electrophile B. The alpha carbon can gain a proton and act like an electrophile and the carbonyl carbon is a nucleophile C. The oxygen of the carbonyl group can attack the carbon of the carbonyl group D. Only esters can undergo self-condensation reactionsarrow_forward
- 71arrow_forwardD10)arrow_forwardBased on the characteristics of the carbonyl group (C = O), what reactions or transformations take place with aldehydes and ketones? a. nucleophilic additions by oxygenb. electrophilic additions by carbon attackc. nucleophilic additions by carbon attackd. electrophilic substitutions through a carbocationand. acid-base because carbonyl can act as both an electrophile and a nucleophilearrow_forward
arrow_back_ios
SEE MORE QUESTIONS
arrow_forward_ios
Recommended textbooks for you
Organic Chemistry: A Guided InquiryChemistryISBN:9780618974122Author:Andrei StraumanisPublisher:Cengage Learning
Organic ChemistryChemistryISBN:9781305580350Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. FootePublisher:Cengage Learning
Chemistry: Matter and ChangeChemistryISBN:9780078746376Author:Dinah Zike, Laurel Dingrando, Nicholas Hainen, Cheryl WistromPublisher:Glencoe/McGraw-Hill School Pub Co
Organic Chemistry: A Guided Inquiry
Chemistry
ISBN:9780618974122
Author:Andrei Straumanis
Publisher:Cengage Learning
Organic Chemistry
Chemistry
ISBN:9781305580350
Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Publisher:Cengage Learning
Chemistry: Matter and Change
Chemistry
ISBN:9780078746376
Author:Dinah Zike, Laurel Dingrando, Nicholas Hainen, Cheryl Wistrom
Publisher:Glencoe/McGraw-Hill School Pub Co
How to Design a Total Synthesis; Author: Chemistry Unleashed;https://www.youtube.com/watch?v=9jRfAJJO7mM;License: Standard YouTube License, CC-BY