Organic Chemistry - Standalone book
10th Edition
ISBN: 9780073511214
Author: Francis A Carey Dr., Robert M. Giuliano
Publisher: McGraw-Hill Education
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Textbook Question
Chapter 8, Problem 27P
Catalytic hydrogenation of 1,4-dimethylcyclopentene yields a mixture of two products.
Identify them. One of them is formed in much greater amounts than the other (observed
ratio =10:1). Which one is the major product?
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conditions.
Part 1 of 2
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8
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Draw the alkene that would react with the reagent given to account for the product formed.
? + H₂O
H₂SO4
CH3
CH3 CHCCH3
OH CH3
• 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
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Chapter 8 Solutions
Organic Chemistry - Standalone book
Ch. 8.1 - What three alkenes yield 2-methylbutane on...Ch. 8.2 - Prob. 2PCh. 8.2 - Prob. 3PCh. 8.3 - Prob. 4PCh. 8.4 - Prob. 5PCh. 8.4 - Give a structural formula for the carbocation...Ch. 8.5 - Prob. 7PCh. 8.6 - Instead of the three-step process of Mechanism...Ch. 8.6 - The rates of hydration of the two alkenes shown...Ch. 8.6 - Is the electrophilic addition of hydrogen chloride...
Ch. 8.7 - You can calculate the equilibrium constant for the...Ch. 8.7 - Does the presence or absence of a catalyst such as...Ch. 8.7 - The gas phase reaction of ethanol with hydrogen...Ch. 8.8 - Prob. 14PCh. 8.8 - Hydroborationoxidation of -pinene, like its...Ch. 8.10 - Arrange the compounds 2-methyl-1-butene,...Ch. 8.10 - Give the structure of the product formed when each...Ch. 8.11 - Prob. 18PCh. 8.11 - Prob. 19PCh. 8.12 - Prob. 20PCh. 8.12 - Prob. 21PCh. 8.13 - Prob. 22PCh. 8.14 - Prob. 23PCh. 8.14 - Prob. 24PCh. 8 - How many alkenes yield...Ch. 8 - Prob. 26PCh. 8 - Catalytic hydrogenation of...Ch. 8 - Prob. 28PCh. 8 - Prob. 29PCh. 8 - Prob. 30PCh. 8 - Prob. 31PCh. 8 - A single epoxide was isolated in 7984% yield in...Ch. 8 - Prob. 33PCh. 8 - Prob. 34PCh. 8 - On catalytic hydrogenation over a rhodium...Ch. 8 - Prob. 36PCh. 8 - Prob. 37PCh. 8 - Prob. 38PCh. 8 - Prob. 39PCh. 8 - 1-Butene has a higher heat of hydrogenation than...Ch. 8 - Match the following alkenes with the appropriate...Ch. 8 - The heats of reaction were measured for addition...Ch. 8 - Complete the following table by adding + and -...Ch. 8 - Match the heats of hydrogenation (107 kJ/mol,...Ch. 8 - The iodination of ethylene at 25 C is...Ch. 8 - Specify reagents suitable for converting...Ch. 8 - (a) Which primary alcohol of molecular formula...Ch. 8 - Identify compounds A and B in the retrosynthesis...Ch. 8 - Identify compounds A and B in the retrosynthesis...Ch. 8 - Prob. 50PCh. 8 - On being heated with a solution of sodium ethoxide...Ch. 8 - Compound A (C7H15Br) is not a primary alkyl...Ch. 8 - Prob. 53PCh. 8 - Prob. 54PCh. 8 - A mixture of three alkenes (A, B, and C) was...Ch. 8 - Reaction of 3,3-dimethyl-1-butene with hydrogen...Ch. 8 - Dehydration of 2,2,3,4,4-pentamethyl-3-pentanol...Ch. 8 - Prob. 58PCh. 8 - East Indian sandalwood oil contains a hydrocarbon...Ch. 8 - Prob. 60PCh. 8 - Prob. 61PCh. 8 - Prob. 62PCh. 8 - Prob. 63PCh. 8 - Prob. 64PCh. 8 - On the basis of the mechanism of acid-catalyzed...Ch. 8 - As a method for the preparation of alkenes, a...Ch. 8 - Which of the following is the most reasonable...Ch. 8 - Prob. 68PCh. 8 - Oxymercuration Concerns about mercurys toxicity...Ch. 8 - Prob. 70DSPCh. 8 - Prob. 71DSPCh. 8 - Prob. 72DSPCh. 8 - Prob. 73DSPCh. 8 - Oxymercuration Concerns about mercurys toxicity...
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- Predict the -elimination product(s) formed when each chloroalkane is treated with sodium ethoxide in ethanol. If two or more products might be formed, predict which is the major product.arrow_forwardDraw the alkene that would react with the reagent given to account for the product formed. ? + H₂O H₂SO4 CH3 CH3CCH3 OH 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 ChemDoodleⓇarrow_forwardWhen 2-bromo-3-phenylbutane is treated with sodium methoxide, two alkenes result (by E2 elimination). The Zaitsevproduct predominates.(a) Draw the reaction, showing the major and minor products.(b) When one pure stereoisomer of 2-bromo-3-phenylbutane reacts, one pure stereoisomer of the major product results.For example, when (2R,3R)-2-bromo-3-phenylbutane reacts, the product is the stereoisomer with the methyl groups cis.Use your models to draw a Newman projection of the transition state to show why this stereospecificity is observed.(c) Use a Newman projection of the transition state to predict the major product of elimination of (2S,3R)-2-bromo-3-phenylbutanearrow_forward
- When 2-bromo-3-phenylbutane is treated with sodium methoxide, two alkenes result (by E2 elimination). The Zaitsevproduct predominates.(a) Draw the reaction, showing the major and minor products.(b) When one pure stereoisomer of 2-bromo-3-phenylbutane reacts, one pure stereoisomer of the major product results.For example, when (2R,3R)-2-bromo-3-phenylbutane reacts, the product is the stereoisomer with the methyl groups cis.Use your models to draw a Newman projection of the transition state to show why this stereospecificity is observedarrow_forwardDraw the organic product that is expected to form when the following compound is oxidized under biological conditions. oxidation SH reduction • You do not have to consider stereochemistry. You do not have to explicitly draw H atoms. • If no reaction occurs, draw the organic starting material.arrow_forwardConsider a reaction where cis-but-2-ene is treated with OsO4 followed by NaHSO3/H2O. Draw the structure of one product that is formed in the reaction, including correct stereochemistry.arrow_forward
- Draw the cycloalkene that would react with the reagent given to account for the product formed. ? + H₂O H₂SO4 CH3 ▼ • 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. » [ ]# CH3 ? OHarrow_forwardConsider a reaction where cis-but-2-ene is treated with sO followed by NaHSO/H, O. Draw the structure of one product that is formed in the reaction, including correct stereochemistry.arrow_forwardCompounds X and Y are both C5H11CI products formed in the radical chlorination of pentane. Base-promoted E2 elimination of X and Y gives, in each case, a single C5H10 alkene (ignoring double bond stereochemistry). Both X and Y react in SN2 fashion with sodium iodide in acetone; Y reacts faster than X. What is the structure of Y? • Do not use stereobonds in your answer. • In cases where there is more than one possible structure for each molecule, just give one for each. • Draw one structure per sketcher. Add additional sketchers using the drop-down menu in the bottom right corner. • Separate structures with + signs from the drop-down menu. ChemDoodle (Previous Nextarrow_forward
- Draw the alkene that would react with the reagent given to account for the product formed. ? + H₂O ● 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. 8 H₂SO4 // CH3 CH3CHCCH3 OH CH3 ? [F Previous Email Instructarrow_forwardCompounds X and Y are both C7H15Cl products formed in the radical chlorination of 2,4-dimethylpentane. Base-promoted E2 elimination of X and Y gives, in each case, a single C7H₁4 alkene. Both X and Y undergo an SN2 reaction with sodium iodide in acetone solution to give C7H15l products; in this reaction Y reacts faster than X. What is the structure of X? • Do not use stereobonds in your answer. • In cases where there is more than one possible structure for each molecule, just give one for each. . Draw one structure per sketcher. Add additional sketchers using the drop-down menu in the bottom right corner. Separate structures with + signs from the drop-down menu. наarrow_forwardМСРВА Alkenes are oxidized to give epoxides on treatment with a peroxyacid, RCO3H, such as metachloroperoxybenzoic acid (MCPBA). Peroxyacids transfer an oxygen atom to the alkene with syn stereochemistry, i.e. both C-O bonds form on the same face of the double bond, through a single step mechanism without intermediates. The oxygen atom farthest from the carbonyl group is the one transferred. Draw curved arrows to show the movement of electrons in this step of the mechanism. Arrow-pushing Instructions H .CI .CI HOarrow_forward
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