Organic Chemistry
7th Edition
ISBN: 9780321803221
Author: Paula Y. Bruice
Publisher: Prentice Hall
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Chapter 10, Problem 51P
cis-1-Bromo-4-tert-butylcyclohexane and trans-1-bromo-4-tert-butylcyclohexane both react with sodium ethoxide in ethanol to form 4-tert-butylcyclohexene. Explain why the cis isomer reacts much more rapidly than the trans isomer.
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Chapter 10 Solutions
Organic Chemistry
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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- Addition of HBr to allene (CH2 = C = CH2) forms 2-bromoprop-1-ene rather than 3-bromoprop-1-ene, even though 3-bromoprop-1-ene is formed from an allylic carbocation. Considering the arrangement of orbitals in the allene reactant, explain this result.arrow_forwardDehydrohalogenation of 1-chloro-1-methylcyclopropane affords two alkenes (A and B) as products. Explain why A is the major product despite the fact that it contains the less substituted double bond.arrow_forwardBelow are the structures for trans-1-chloro-2-t-butylcyclohexane and cis-1- chloro-2-t-butylcyclohexane. Both molecules can react with a base to form an alkene. cis-1-chloro-2-t-butylcyclohexane reacts 10x faster than trans-1-chloro2-t-butylcyclohexane. Use chair conformations to explain why the cis isomer is more reactive.arrow_forward
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