Organic Chemistry
7th Edition
ISBN: 9780321803221
Author: Paula Y. Bruice
Publisher: Prentice Hall
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Textbook Question
Chapter 10.3, Problem 5P
Four
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When 2-bromobutane is reacted with CH3O-, two alkene products, namely 2-butene and 1-butene are obtained. Explain why the E2 reaction produces 2-butene as the major product (80%) and 1-butene as the minor product (20%)
You are required to synthesize 2-bromopentane from the reaction between an alkene with HBr. Which alkene, 1-pentene or 2-pentene, should you react with HBr in order to get 2-bromopentane? Give an explanation.
Draw the major organic product formed by reaction of 2-hexyne with the following reagent: H₂O in H₂SO4
/ HgSO4.
• Consider E/Z stereochemistry of alkenes.
• In cases where there is more than one answer, just draw one.
• If no reaction occurs, draw the organic starting material.
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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- Draw the product that would form when 4-methyl-2-pentene reacts with bromine. • You do not have to consider stereochemistry. • You do not have to explicitly draw H atoms. • In cases where there is more than one answer, just draw one. / Sn [F ? ChemDoodlearrow_forwardHydroxylation of E-2-pentene with osmium tetroxide yields a different product than the same reaction using the Z configuration. Draw the structures of the alkenes and show the stereochemistry for each product. Explain any differences between them.arrow_forwardSuppose that the alkene in Figure 9 reacts with 1 mole of hydrogen chloride. Predict the structure of the main product of the reaction.arrow_forward
- 1. You are planning to carry out a reaction between butyne CH3CH₂C=CH, and sodium methoxide, CH3ONa. You also need to choose an appropriate solvent for the reaction. Would H₂O be an appropriate solvent? Explain your rationale.arrow_forwardWhat is the product in the hydroboration/oxidation of (E)-3-methylhex-3-ene? Draw its structure.arrow_forwardDraw the major organic product formed by reaction of 2-hexyne with the following reagent: BH3 followed by CH3COOH. . Consider E/Z stereochemistry of alkenes. In cases where there is more than one answer, just draw one. • If no reaction occurs, draw the organic starting material.arrow_forward
- 7) 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_forward3. What are the product/s formed from the nucleophilic substitution of 3-chloro-1,2-epoxycyclopentane with methanol followed by reaction with water? Draw the chemical reaction (structural formula) inside the boxes.arrow_forward1. b) Show the MECHANISM for the POLAR addition of molecular chlorine to cyclopentane. c) The reaction of toluene and ethylbenzene was through the alkyl groups, -CH 3 and -CH 2 CH 3, respectively. Why didn’t xylene, which has TWO methyl groups, react with bromine in the time allotted?arrow_forward
- 2. The following carbocation is generated as an intermediate in the addition of H-Br to an alkene. Draw the structure of all possible alkenes that could have formed this intermediate.arrow_forwardDefine the E2 mechanism for the Preparation of Alkenes ?arrow_forward(dehydrobromination) A chemist carried out an elimination reaction of 1,1-dimethyl-2- bromocyclopentane. The chemist expected the reaction to yield alkene Z as product. However, alkene Z DID NOT form. Instead, three alkenes were produced: one alkene was the major product, the other two alkenes was the minor products. What was the major alkene product that formed? Br Select one: A. I B. II C. IV D. III alcohol HEAT || Z = + (HBr) IVarrow_forward
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