ORGANIC CHEMISTRY W/CONNECT & ALEKS
6th Edition
ISBN: 9781264683888
Author: SMITH
Publisher: MCG
expand_more
expand_more
format_list_bulleted
Textbook Question
Chapter 21, Problem 39P
Explain why
Expert Solution & Answer
Want to see the full answer?
Check out a sample textbook solutionStudents have asked these similar questions
Explain why methyl trifluoroacetate, CF3CO2CH3, is more reactive than methyl acetate, CH3CO2CH3, in nucleophilic acyl substitution reactions.
Cyclohexane-1,3-dione is a diketone that can act as a Brønsted-Lowry acid despite not having a hydrogen bonded to an electronegative atom. In this molecule, a hydrogen bonded to carbon 2 is acidic. Hexanol is an alcohol and hence can also act as a Brønsted-Lowry acid.
a) Draw the stabilized conjugate bases of cyclohexane-1,3-dione and hexanol. No need to draw the protonated forms.
b) Based on your illustration in part (a), predict which one has a lower pKa between cyclohexane-1,3-dione and hexanol. Explain why.
A) Provide four different ways that 2-methylpropanal could be made from an alkene,
an alcohol, an ester and an acetal in a single step.
an alkene
H
an alcohol
2-methylpropanal
an ester
an acetal
Chapter 21 Solutions
ORGANIC CHEMISTRY W/CONNECT & ALEKS
Ch. 21.2 - Problem 23.1 Draw the enol or keto tautomer(s) of...Ch. 21.2 - Problem 23.3 When phenylacetaldehyde is dissolved...Ch. 21.3 - Prob. 5PCh. 21.3 - Problem 23.5 Which bonds in the following...Ch. 21.3 - Prob. 7PCh. 21.3 - Prob. 8PCh. 21.3 - Prob. 9PCh. 21.4 - Prob. 10PCh. 21.5 - Prob. 11PCh. 21.7 - Problem 23.11 Draw the products of each...
Ch. 21.7 - Problem 23.12 Draw the products of each reaction....Ch. 21.7 - Prob. 14PCh. 21.7 - Prob. 15PCh. 21.8 - Prob. 16PCh. 21.8 - Prob. 17PCh. 21.8 - Prob. 18PCh. 21.8 - Problem 23.18 How can pentan-2-one be converted...Ch. 21.8 - Problem 23.19 Identify A, B, and C, intermediates...Ch. 21.9 - Problem 23.20 Which of the following compounds...Ch. 21.9 - Problem 23.21 Draw the products of each...Ch. 21.9 - Prob. 23PCh. 21.9 - Prob. 24PCh. 21.9 - Prob. 25PCh. 21.10 - Prob. 26PCh. 21.10 - Prob. 27PCh. 21.10 - Prob. 28PCh. 21.10 - Prob. 29PCh. 21 - 23.29 Draw enol tautomer(s) for each compound....Ch. 21 - 22.30 The cis ketone A is isomerized to a trans...Ch. 21 - 23.31 Draw enol tautomer(s) for each compound.
...Ch. 21 - Prob. 33PCh. 21 - Prob. 34PCh. 21 - 23.35 Rank the labeled protons in each compound in...Ch. 21 - Prob. 36PCh. 21 - Prob. 37PCh. 21 - 23.38 Acyclovir is an effective antiviral agent...Ch. 21 - 23.39 Explain why forms two different alkylation...Ch. 21 - Prob. 40PCh. 21 - 23.42 Draw a stepwise mechanism for the following...Ch. 21 - Prob. 42PCh. 21 - Prob. 43PCh. 21 - 23.45 Devise a synthesis of valproic acid , a...Ch. 21 - Prob. 57PCh. 21 - 23.57 Draw a stepwise mechanism showing how two...Ch. 21 - 23.58 Draw a stepwise mechanism for the following...Ch. 21 - Prob. 65PCh. 21 - 23.66 Synthesize (Z)-hept-5-en-2-one from ethyl...
Knowledge Booster
Learn more about
Need a deep-dive on the concept behind this application? Look no further. Learn more about this topic, chemistry and related others by exploring similar questions and additional content below.Similar questions
- A problem often encountered in the oxidation of primary alcohols to acids is that esters are sometimes produced as by-products. For example, oxidation of ethanol yields acetic acid and ethyl acetate: Propose a mechanism to account for the formation of ethyl acetate. Take into account the reversible reaction between aldehydes and alcohols:arrow_forwardExplain two different ways to introduce an alkyl group on a benzene ring ?arrow_forwardHydration of aldehydes and ketones can be catalyzed by acid or base. Bases catalyze hydration by: protonating the carbonyl oxygen making the carbonyl group more electrophilic employing hydroxide ion, which is a better nucleophile than water making the carbonyl group less electrophilic shifting the equilibrium position of the reaction to favor productsarrow_forward
- Draw the overall reaction of 2-bromo-2-methylpropane with H2O to give the alcohol product. Include all by-products that form.arrow_forwardAcid-catalyzed dehydration of 3-methyl-2-pentanol gives three alkenes: 3-methyl-1-pentene, 3-methyl-2-pentene, and 3-methylenepentane. Draw the structure of the carbocation intermediate leading to the formation of 3-methyl-2-pentene.arrow_forward1-Octen-3-ol is a potent mosquito attractant commonly used in mosquito traps. A number of reactions, including hydrogenation, will transform 1-octen-3-ol into a less effective molecule. Draw the structure of a hydrogenation product of 1-octen-3-ol.arrow_forward
- Describe the procedures on how will you prepare an alcohol from an alkene.arrow_forwardhelparrow_forwardAcetal derivatives of aldehydes and ketones are prepared by an acid-catalyzed dehydration reaction with alcohols or diols. Using more pictures than words, draw a reaction and a mechanism that shows the formation of acetal.arrow_forward
- 1. The acid-catalyzed elimination of an alcohol is an equilibrium reaction and requires special reac- tion conditions to favour the formation of the alkene product. What chemical principle controls the amount of alkene product that is produced? Provide two laboratory techniques that can be used to obtain good alkene yields in alcohol elimination reactions.arrow_forwardWhen trans-2-chloro-1-cyclohexanol is treated with a base, cyclohexene oxide is the product. However, when cis-2-chloro-1-cyclohexanol is treated with a base, the product is cyclohexanone. Write the mechanism for each of the two reactions.arrow_forwarda)Step by step show the reaction of 1 mol of water from the 3,3-dimethyl-2-pentanol compound in acid-catalyzed medium.Name the main product formed. b)Indicate whether the resulting product shows the geometric isomer or not. c)Write the products formed when the product is ozonized and oxidized.arrow_forward
arrow_back_ios
SEE MORE QUESTIONS
arrow_forward_ios
Recommended textbooks for you
- Organic ChemistryChemistryISBN:9781305580350Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. FootePublisher:Cengage LearningOrganic Chemistry: A Guided InquiryChemistryISBN:9780618974122Author:Andrei StraumanisPublisher:Cengage Learning
- Chemistry for Today: General, Organic, and Bioche...ChemistryISBN:9781305960060Author:Spencer L. Seager, Michael R. Slabaugh, Maren S. HansenPublisher:Cengage Learning
Organic Chemistry
Chemistry
ISBN:9781305580350
Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Publisher:Cengage Learning
Organic Chemistry: A Guided Inquiry
Chemistry
ISBN:9780618974122
Author:Andrei Straumanis
Publisher:Cengage Learning
Chemistry for Today: General, Organic, and Bioche...
Chemistry
ISBN:9781305960060
Author:Spencer L. Seager, Michael R. Slabaugh, Maren S. Hansen
Publisher:Cengage Learning
07 Physical Properties of Organic Compounds; Author: Mindset;https://www.youtube.com/watch?v=UjlSgwq4w6U;License: Standard YouTube License, CC-BY