Organic Chemistry (8th Edition)
8th Edition
ISBN: 9780134042282
Author: Paula Yurkanis Bruice
Publisher: PEARSON
expand_more
expand_more
format_list_bulleted
Concept explainers
Textbook Question
Chapter 9.11, Problem 37P
Which isomer reacts more rapidly in an E2 reaction: cis-l·bromo-4-tert-butylcyclohexane or trans-1-bromo-4-tert·butylcyclohexane? Explain your answer.
Expert Solution & Answer
Want to see the full answer?
Check out a sample textbook solutionStudents have asked these similar questions
Consider 3-iodo-2,3-dimethylpentane and 3-iodo-2methylpentane.
a. which reacts faster in an Sn2 reaction? Explain.
b. which reacts faster in an E2 reaction? Explain.
3-bromo-1-pentene and 1-bromo-2-pentene undergo SN1 reaction at almost the same rate, but one is a secondary halide while the other is a primary halide. Explain your answer. Then,
decide which the following compounds will react faster in an E2 reaction; trans-1-bromo-2-isopropylcyclohexane or cis-1-bromo-2-isopropylcyclohexane.
and Explain your answer.
Rank the alkyl halides in each group in order of increasing reactivity in an E2 reaction.
Chapter 9 Solutions
Organic Chemistry (8th Edition)
Ch. 9.1 - Prob. 3PCh. 9.1 - Does increasing the energy barrier for an SN2...Ch. 9.1 - Rank the following alkyl bromides from most...Ch. 9.1 - Prob. 8PCh. 9.2 - Prob. 9PCh. 9.2 - Prob. 10PCh. 9.2 - Prob. 11PCh. 9.2 - Prob. 12PCh. 9.2 - Which substitution reaction lakes place more...Ch. 9.2 - Prob. 15P
Ch. 9.2 - Prob. 17PCh. 9.3 - Prob. 18PCh. 9.4 - Prob. 19PCh. 9.5 - Draw the configuration(s) of the substitution...Ch. 9.5 - Which of the following reactions take place more...Ch. 9.7 - Prob. 22PCh. 9.7 - Prob. 23PCh. 9.7 - Prob. 24PCh. 9.7 - Prob. 25PCh. 9.8 - Four alkenes are formed from the E1 reaction of...Ch. 9.8 - If 2-fluoropentane could undergo an E1 reaction,...Ch. 9.8 - Prob. 28PCh. 9.8 - Propose a mechanism for the following reaction:Ch. 9.9 - Prob. 30PCh. 9.9 - What percentage of the reaction described in...Ch. 9.10 - Prob. 33PCh. 9.10 - Prob. 35PCh. 9.11 - Why do cis-1-bromo-2-ethylcyclohexane and...Ch. 9.11 - Which isomer reacts more rapidly in an E2...Ch. 9.11 - Prob. 38PCh. 9.12 - Prob. 39PCh. 9.12 - Prob. 40PCh. 9.12 - Prob. 41PCh. 9.12 - Explain why only a substitution product and no...Ch. 9.12 - a. Explain why 1-bromo-2,2-dimethylpropane has...Ch. 9.13 - Prob. 44PCh. 9.13 - Prob. 45PCh. 9.13 - What products will be obtained from the El...Ch. 9.13 - Prob. 47PCh. 9.13 - Prob. 48PCh. 9.13 - Prob. 49PCh. 9.13 - Why is a cumulated diene not formed in the...Ch. 9.13 - What product is obtained when the following...Ch. 9.13 - What products are formed from the following...Ch. 9.14 - Prob. 54PCh. 9.14 - Prob. 55PCh. 9.14 - Prob. 56PCh. 9.14 - Prob. 58PCh. 9.14 - Under which of the following reaction conditions...Ch. 9.15 - A small amount of another organic product is...Ch. 9.15 - What is the best way to prepare the following...Ch. 9.15 - Prob. 62PCh. 9.15 - What products (including stereoisomers, if...Ch. 9.16 - After a proton is removed from the OH group, which...Ch. 9.16 - Prob. 65PCh. 9.17 - Prob. 66PCh. 9 - Prob. 1PCh. 9 - Methoxychlor is an insecticide that was intended...Ch. 9 - Prob. 67PCh. 9 - Prob. 68PCh. 9 - Prob. 69PCh. 9 - Prob. 70PCh. 9 - Prob. 71PCh. 9 - Prob. 72PCh. 9 - Starting with cyclohexene, how can the following...Ch. 9 - Prob. 74PCh. 9 - The pKa of acetic acid in water is 4.76. What...Ch. 9 - Prob. 76PCh. 9 - Prob. 77PCh. 9 - Prob. 78PCh. 9 - Prob. 79PCh. 9 - Prob. 80PCh. 9 - Prob. 81PCh. 9 - Prob. 82PCh. 9 - Draw the major product obtained when each of the...Ch. 9 - Prob. 84PCh. 9 - a. Indicate how each of the following factors...Ch. 9 - Prob. 86PCh. 9 - A chemist wanted to synthesize the...Ch. 9 - Prob. 88PCh. 9 - Prob. 89PCh. 9 - Prob. 90PCh. 9 - Prob. 91PCh. 9 - Starting with an alkyl halide, how could the...Ch. 9 - Indicate which species in each pair gives a higher...Ch. 9 - Prob. 94PCh. 9 - Rank the following from most reactive to least...Ch. 9 - For each of the following alkyl halides, indicate...Ch. 9 - Prob. 97PCh. 9 - When 2-bromo-2,3-dimethylbutane reacts with a...Ch. 9 - Prob. 100PCh. 9 - When the following compound undergoes solvolysis...Ch. 9 - cis-1-Bromo-4-tert-butylcyclohexane and...Ch. 9 - Draw the substitution and elimination products.Ch. 9 - tert-Butyl chloride undergoes solvolysis in both...Ch. 9 - Prob. 105PCh. 9 - Prob. 106PCh. 9 - In which solventethanol or diethyl etherwould the...Ch. 9 - Prob. 108PCh. 9 - Two bromoethers are obtained from the reaction of...Ch. 9 - Prob. 110PCh. 9 - Prob. 111PCh. 9 - Prob. 112PCh. 9 - Which of the following hexachlorocyclohexanes is...Ch. 9 - Explain why the rate of the reaction of...Ch. 9 - Prob. 115PCh. 9 - Two elimination products are obtained from the...Ch. 9 - Draw the structures or the product of the obtained...Ch. 9 - How could you prepare the following compounds from...Ch. 9 - cis-4-Bromocyclohexanol and...Ch. 9 - Prob. 120PCh. 9 - Propose a mechanism for the following reaction:Ch. 9 - Prob. 122PCh. 9 - Prob. 123PCh. 9 - Prob. 124PCh. 9 - Prob. 125PCh. 9 - Predict the product for the following reaction and...Ch. 9 - Prob. 127PCh. 9 - Prob. 128PCh. 9 - When equivalent amounts of methyl bromide nod...Ch. 9 - Prob. 130PCh. 9 - The reaction of chloromethane with hydroxide ion...
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
- Consider the E1 reaction of 3-bromo-2-cyclohexyl-butane. How many elimination products are possible? Include (E)/(Z) isomers as separate products.arrow_forwardThe reaction of cyclopentanol with HBr will most likely proceed via: a. E2 b. E1 c. SN1 d. E1cb e. SN2arrow_forwardThere are two benzylic bromides that give (Z)-4,6-dimethyl-3-phenyl-3-heptene on E2 elimination. Draw them.arrow_forward
- List the following alkyl halides in order of decreasing reactivity toward SN1/E1 reactions (from 1: most reactive to 4: least reactive).arrow_forwardDraw a stepwise mechanism for the following reaction that illustrates how two substitution products are formed. Explain why 1-bromohex-2ene reacts rapidly with a weak nucleophile (CH3OH) under SN1 reaction conditions, even though it is a 1 ° alkyl halide.arrow_forwardArrange the following alkyl halides in increasing reactivity in E1 reaction. Write 1 for the least reactive, then 2 and 3 for the most reactive A. 2,3-dimethyl-2-chloro-hexane B. 5-ethyl-3,3-dimethyl-1-chloroheptane C. 4-bromo-1-ethyl-2-nitrocyclohexane Answer: A. ____ B. ____ C. ____arrow_forward
- a. Explain why 1-bromo-2,2-dimethylpropane has difficulty undergoing both SN2 and SN1 reactions. b. Can it undergo E2 and E1 reactions?arrow_forwardDraw a stepwise mechanism for the following reaction that illustrates how two substitution products are formed. Explain why 1-bromohex-2-ene reacts rapidly with a weak nucleophile (CH3OH) under SN1 reaction conditions, even though it is a 1° alkyl halide.arrow_forwardWhat alkenes are formed from each alkyl halide by an E1 reaction? Use the Zaitsev rule to predict the major product.arrow_forward
- Which compound reacts fastest in an E1 rxn. The correct answer is C but explain why it is correct and why the other options are incorrect. thanks :)arrow_forwardThe Hofmann product is favored by the E2 mechanism when 2-bromo-3-methylbutane is added: A. MeOH B. MeO:- in MeOH C. Nal in acetona D. (CH 3)3 CO:- in (CH 3),COHarrow_forwardWhat alkene is the major product formed from each alkyl halide in an E1 reaction?arrow_forward
arrow_back_ios
SEE MORE QUESTIONS
arrow_forward_ios
Recommended textbooks for you
- Organic ChemistryChemistryISBN:9781305580350Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. FootePublisher:Cengage Learning
Organic Chemistry
Chemistry
ISBN:9781305580350
Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Publisher:Cengage Learning
IR Spectroscopy; Author: Professor Dave Explains;https://www.youtube.com/watch?v=_TmevMf-Zgs;License: Standard YouTube License, CC-BY