Organic Chemistry (Looseleaf) - With Access
7th Edition
ISBN: 9780134325774
Author: Bruice
Publisher: PEARSON
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Textbook Question
Chapter 10.7, Problem 17P
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.
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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 10 Solutions
Organic Chemistry (Looseleaf) - With Access
Ch. 10.2 - Prob. 1PCh. 10.2 - Prob. 2PCh. 10.2 - Prob. 3PCh. 10.2 - Prob. 4PCh. 10.3 - Four alkenes are formed from the E1 reaction of...Ch. 10.3 - If 2-fluoropentane could undergo an E1 reaction,...Ch. 10.3 - Prob. 7PCh. 10.3 - Propose a mechanism for the following reaction:Ch. 10.4 - Prob. 9PCh. 10.4 - What products will be obtained from the El...
Ch. 10.4 - Prob. 11PCh. 10.5 - Prob. 12PCh. 10.6 - Prob. 14PCh. 10.7 - Why do cis-1-bromo-2-ethylcyclohexane and...Ch. 10.7 - Which isomer reacts more rapidly in an E2...Ch. 10.7 - Prob. 18PCh. 10.8 - Prob. 19PCh. 10.8 - Prob. 20PCh. 10.9 - Prob. 21PCh. 10.9 - Explain why only a substitution product and no...Ch. 10.9 - Prob. 23PCh. 10.9 - Prob. 24PCh. 10.9 - Prob. 25PCh. 10.9 - a. Explain why 1-bromo-2,2-dimethylpropane has...Ch. 10.10 - A small amount of another organic product is...Ch. 10.10 - What is the best way to prepare the following...Ch. 10.10 - Prob. 29PCh. 10.10 - Prob. 30PCh. 10.10 - Why is a cumulated diene not formed in the...Ch. 10.10 - What product is obtained when the following...Ch. 10.11 - Prob. 33PCh. 10.11 - Prob. 34PCh. 10 - Draw the major product obtained when each of the...Ch. 10 - Prob. 36PCh. 10 - a. Indicate how each of the following factors...Ch. 10 - Prob. 38PCh. 10 - A chemist wanted to synthesize the...Ch. 10 - Prob. 40PCh. 10 - Prob. 41PCh. 10 - Prob. 42PCh. 10 - Starting with an alkyl halide, how could the...Ch. 10 - Indicate which species in each pair gives a higher...Ch. 10 - Prob. 45PCh. 10 - For each of the following alkyl halides, indicate...Ch. 10 - Prob. 47PCh. 10 - When 2-bromo-2,3-dimethylbutane reacts with a...Ch. 10 - Prob. 49PCh. 10 - When the following compound undergoes solvolysis...Ch. 10 - cis-1-Bromo-4-tert-butylcyclohexane and...Ch. 10 - Draw the substitution and elimination products.Ch. 10 - Prob. 53PCh. 10 - Prob. 54PCh. 10 - Which of the following hexachlorocyclohexanes is...Ch. 10 - Explain why the rate of the reaction of...Ch. 10 - Prob. 57PCh. 10 - Two elimination products are obtained from the...Ch. 10 - Draw the structures or the product of the obtained...Ch. 10 - How could you prepare the following compounds from...Ch. 10 - cis-4-Bromocyclohexanol and...Ch. 10 - Prob. 62PCh. 10 - Prob. 63P
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- 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
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- 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
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