Introduction to General, Organic and Biochemistry
12th Edition
ISBN: 9780357119303
Author: Bettelheim, Frederick A., Brown, William H., Campbell, Mary K., FARRELL, Shawn O., Torres, Omar
Publisher: Cengage Learning
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Chapter 12.5, Problem 12.9QC
Problem 12-9
Propose a three-step reaction mechanism for the acid-catalyzed hydration of 1-methylcyclohexene to give 1-methylcyclohexanol.
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PROBLEM 10-15
Show how you would synthesize each tertiary alcohol by adding an appropriate Grignard
reagent to a ketone.
(a) 3-phenylhexan-3-ol (3 ways) (b) Ph3COH
(c) 1-ethylcyclopentanol
(d)
2-cyclopentylpentan-2-ol
PROBLEM 14-27Predict the major products of the following reactions, including stereochemistry whereappropriate.2,2-dimethyloxirane + H18O- >H218O
PROBLEM 18-28(a) Propose a mechanism for the acid-catalyzed reaction of cyclohexanone with ethyleneglycol to give cyclohexanone ethylene acetal.(b) Propose a mechanism for the acid-catalyzed hydrolysis of cyclohexanone ethylene acetal.(c) Compare the mechanisms you drew in parts (a) and (b). How similar are these mechanisms,comparing them in reverse order?
Chapter 12 Solutions
Introduction to General, Organic and Biochemistry
Ch. 12.3 - Prob. 12.1QCCh. 12.3 - Prob. 12.2QCCh. 12.3 - Problem 12-3 Write the IUPAC name for each...Ch. 12.3 - Problem 12-4 Draw structural formulas for the...Ch. 12.3 - Problem 12-5 How many stereoisomers are possible...Ch. 12.5 - Prob. 12.6QCCh. 12.5 - Problem 12-7 Propose a two-step mechanism for the...Ch. 12.5 - Prob. 12.8QCCh. 12.5 - Problem 12-9 Propose a three-step reaction...Ch. 12.5 - Prob. 12.10QC
Ch. 12.8 - Prob. 12.11QCCh. 12 - Prob. 1PCh. 12 - Answer true or false. Both ethylene and acetylene...Ch. 12 - 12-13 What is the difference in structure between...Ch. 12 - There are three compounds with the molecular...Ch. 12 - 12-15 Name and draw structural formulas for all...Ch. 12 - Prob. 6PCh. 12 - Draw a structural formula for at least one...Ch. 12 - Each carbon atom in ethane and in ethylene is...Ch. 12 - Prob. 9PCh. 12 - Prob. 10PCh. 12 - Prob. 11PCh. 12 - 12*22 Draw a structural formula for each compound....Ch. 12 - 12-23 Draw a structural formula for each compound....Ch. 12 - Prob. 14PCh. 12 - 12-25 Write the IUPAC name for each unsaturated...Ch. 12 - Explain why each name is incorrect and then write...Ch. 12 - 12-27 Explain why each name is incorrect and then...Ch. 12 - Prob. 18PCh. 12 - 12-29 Which of these alkenes show cis-trans...Ch. 12 - 12-30 Which of these alkenes shows cis-trans...Ch. 12 - 12-31 Cyclodecene exists as both cis and trans...Ch. 12 - Arachidonic acid is a naturally occurring C„o...Ch. 12 - Prob. 23PCh. 12 - If you examine the structural formulas for the...Ch. 12 - 12*35 For each molecule that shows eis-trans...Ch. 12 - Name and draw structural formulas for all...Ch. 12 - /3-Ocimene, a triene found in the fragrance of...Ch. 12 - Answer true or false. Alkenes and alkynes are...Ch. 12 - Prob. 29PCh. 12 - 12-40 Define alkene addition reaction. Write an...Ch. 12 - Prob. 31PCh. 12 - 12-42 Complete these equations.Ch. 12 - Draw structural formulas for all possible...Ch. 12 - Prob. 34PCh. 12 - 12-45 Draw a structural formula for the product of...Ch. 12 - Draw a structural formula for an alkene with the...Ch. 12 - 12-47 Draw a structural formula for an alkene with...Ch. 12 - Draw a structural formula for an alkene with the...Ch. 12 - Prob. 39PCh. 12 - 12-50 Draw the structural formula of an alkene...Ch. 12 - Prob. 41PCh. 12 - Prob. 42PCh. 12 - Following is the structural formula of...Ch. 12 - Propose an explanation for the following...Ch. 12 - There are nine alkenes with the molecular formula...Ch. 12 - Prob. 46PCh. 12 - 12-57 Hydrocarbon A, Cf,Hs, reacts with 2 moles of...Ch. 12 - 12-58 Show how to convert ethylene to these...Ch. 12 - 12-59 Show how to convert 1-butene to these...Ch. 12 - Prob. 50PCh. 12 - 12-61 (Chemical Connections 12A) What is one...Ch. 12 - Prob. 52PCh. 12 - Prob. 53PCh. 12 - 12-64 (Chemical Connections 120 What is the...Ch. 12 - (Chemical Connections 120 Assume that 1 X IO-12 g...Ch. 12 - Prob. 56PCh. 12 - Prob. 57PCh. 12 - Prob. 58PCh. 12 - Prob. 59PCh. 12 - Prob. 60PCh. 12 - Prob. 61PCh. 12 - Suppose you have unlabeled bottles of benzene and...Ch. 12 - Prob. 63PCh. 12 - Prob. 64PCh. 12 - Answer true or false. (a) Phenols and alcohols...Ch. 12 - Prob. 66PCh. 12 - Prob. 67PCh. 12 - Prob. 68PCh. 12 - Prob. 69PCh. 12 - 12-67 (Chemical Connections 12D ) In which isomer...Ch. 12 - Prob. 71PCh. 12 - Prob. 72PCh. 12 - Prob. 73PCh. 12 - Prob. 74PCh. 12 - Prob. 75PCh. 12 - Prob. 76PCh. 12 - Prob. 77PCh. 12 - Prob. 78PCh. 12 - Prob. 79PCh. 12 - Prob. 80PCh. 12 - Prob. 81PCh. 12 - Prob. 82PCh. 12 - Prob. 83PCh. 12 - Prob. 84PCh. 12 - Prob. 85PCh. 12 - Prob. 86PCh. 12 - Propose a structural formula for the product!s)...Ch. 12 - Prob. 88PCh. 12 - Draw the structural formula of an alkene that...Ch. 12 - 12-77 Show how to convert cyclopentene into these...Ch. 12 - Prob. 91PCh. 12 - Prob. 92PCh. 12 - Prob. 93PCh. 12 - Prob. 94PCh. 12 - Prob. 95PCh. 12 - In omega-3 fatty adds, the last carbon of the last...Ch. 12 - Prob. 97PCh. 12 - Prob. 98P
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- Problem 12-7 Propose a two-step mechanism for the addition of HBr to 1-methylcyclohexene to give 1-bromo-l-methylcyclohexane.arrow_forwardPROBLEM 10-14 Show two ways you could synthesize each of the following secondary alcohols by adding an appropriate Grignard reagent to an aldehyde. (b) (a) OH OH (c) H OHarrow_forwardProblem 17-6 Show the reaction of benzaldehyde with one molecule of methanol to form a hemiacetal and then with a second molecule of methanol to form an acetal.arrow_forward
- PROBLEM 18-9Show how the following transformations may be accomplished in good yield. You mayuse any additional reagents that are needed. benzoic acid S phenyl cyclopentyl ketonearrow_forwardPROBLEM 8 -10 What alkenes might be used to prepare the following alcohols by hydroboration-oxidation? (a) CH3 (b) НзС ОН (c) .CH2OH CH3CHCH,CH2OH CH3CHCHCH3arrow_forwardProblem 13 of 14 Submit A common ketone starting material is shown below. Predict the major product for each reaction based on the reagents given. Ignore any inorganic byproducts. Select to Draw = Select to Draw H3O+ NaCN, HCI O Q 1. PhCCNa 2. H3O+ NH2NH2, TSOHarrow_forward
- Problem 14-3 Draw structural formulas for the alkenes formed by the acid-catalyzed dehydration of each alcohol. For each part, predict which alkene will be the major product. (a) 2-Methyl-2-butanol (b) 1-Methylcyclopentanolarrow_forwardProblem 10-15 Show how you would synthesize each tertiary alcohol by adding an appropriate Grignard reagent to a ketone. a. 3-phenylhexan-3-ol (3 ways) b. Ph3 COH c. 1-ethylcyclopentanol d. 2-cyclopentylpentan-2-olarrow_forwardProblem 13 of 20 H₂C Draw the product of the E2 reaction shown below. Include the correct stereochemistry. Ignore any inorganic byproducts. Ph H Br Ph CH3 NaNH2 Draw the E2 Product 34 Q Submitarrow_forward
- PROBLEM 11-3We have covered several oxidants that use a multi-valent atom (Cr, Cl, S, or I) as theiractive species, going from a higher oxidation state before the oxidation to a lower oxidation state after oxidizing the alcohol. Draw the structure of the following atoms, beforeand after the oxidation of an alcohol to a ketone or aldehyde. How many bonds to oxygendoes each atom have before and after the oxidation? the carbinol C in the alcohol that is oxidizedarrow_forwardPROBLEM 4-4 Free-radical chlorination of hexane gives very poor yields of 1-chlorohexane, while cyclohexane can be converted to chlorocyclohexane in good yield. (a) How do you account for this difference? (b) What ratio of reactants (cyclohexane and chlorine) would you use for the synthesis of chlorocyclohexane?arrow_forwardCan you please help with b and c . Thank you !arrow_forward
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