EP ORGANIC CHEMISTRY -MOD.MASTERING 18W
9th Edition
ISBN: 9780136781776
Author: Wade
Publisher: PEARSON CO
expand_more
expand_more
format_list_bulleted
Question
Chapter 11, Problem 11.61SP
Interpretation Introduction
Interpretation: The rate limiting step is to be predicted and an explanation for large difference in
Concept introduction: In a
To determine: The step that is rate limiting and an explanation for large difference in rates of reaction of the given compounds.
Expert Solution & Answer
Want to see the full answer?
Check out a sample textbook solution
Students have asked these similar questions
Acid-catalyzed dehydration of secondary and tertiary alcohols proceeds through an E1 mechanism. The
first step is the protonation of the alcohol oxygen to form an oxonium ion.
Dehydration of 3-methyl-2-butanol forms one major and two minor organic products. Draw the structures,
including hydrogen atoms, of the three organic products of this reaction.
н
н
:бн
н
Нас.
Нас.
CHз
CH3
ČH3
CH3
3-methyl-2-butanol
an oxonium ion
Major Product
Minor Product
Minor Product
Aldehydes and ketones react with one molecule of an alcohol to form compounds called hemiacetals, in which there is one hydroxyl group and one ether-like group. Reaction of a hemiacetal with a second
molecule of alcohol gives an acetal and a molecule of water.
ROH, H+
OH
OR
Aldehyde/ketone
Alcohol
ROH, H+
Draw the structural formulas for the hemiacetal and the acetal formed between the following compounds:
OH
OH
OR
OR
• Use the wedge/hash bond tools to indicate stereochemistry where it exists.
+ H₂O
What is the slow, rate-determining step, in the acid-catalyzed dehydration of 2-
butanol?
Loss of a b-hydrogen from the carbocation to form an alkene.
Protonation of the alcohol to form an oxonium ion.
Loss of water from the oxonium ion to form a carbocation.
The simultaneous loss of a B-hydrogen and water from the oxonium ion.
Chapter 11 Solutions
EP ORGANIC CHEMISTRY -MOD.MASTERING 18W
Ch. 11.1 - Prob. 11.1PCh. 11.2C - Prob. 11.2PCh. 11.3 - Prob. 11.3PCh. 11.3 - Prob. 11.4PCh. 11.3 - Prob. 11.5PCh. 11.3 - Suggest the most appropriate method for each of...Ch. 11.4 - A chronic alcoholic requires a much larger dose of...Ch. 11.4 - Unlike ethylene glycol, propylene glycol...Ch. 11.5 - Predict the major products of the following...Ch. 11.5 - Show how you would convert propan-1-ol to the...
Ch. 11.6 - Predict the products of the following reactions....Ch. 11.7A - Propose a mechanism for the reaction of a....Ch. 11.7B - Prob. 11.13PCh. 11.7B - Show how you would use a simple chemical test to...Ch. 11.7C - Neopentyl alcohol, (CH3)3CCH2OH, reacts with...Ch. 11.7C - Prob. 11.16PCh. 11.7C - When cis-2-methylcyclohexanol reacts with the...Ch. 11.8 - Prob. 11.18PCh. 11.9 - Prob. 11.19PCh. 11.9 - Prob. 11.20PCh. 11.9 - Prob. 11.21PCh. 11.10A - Prob. 11.22PCh. 11.10A - Some alcohols undergo rearrangement or other...Ch. 11.10B - Prob. 11.24PCh. 11.10B - Explain why the acid-catalyzed condensation is a...Ch. 11.10B - Prob. 11.26PCh. 11.10B - When the following substituted cycloheptanol...Ch. 11.11A - Prob. 11.28PCh. 11.11A - Prob. 11.29PCh. 11.11B - Predict the products formed by periodic acid...Ch. 11.12 - Prob. 11.31PCh. 11.13A - Prob. 11.32PCh. 11.14 - Prob. 11.33PCh. 11.14 - a. Show how ethanol and cyclohexanol may be used...Ch. 11.14 - Prob. 11.35PCh. 11.14 - Phenols (pKa 10) are more acidic than other...Ch. 11.14 - To practice working through the early parts of a...Ch. 11.14 - Prob. 11.38PCh. 11 - Predict the major products of the following...Ch. 11 - Show how you would convert 2-methylcyclopentanol...Ch. 11 - In each case, show how you would synthesize the...Ch. 11 - Prob. 11.42SPCh. 11 - Prob. 11.43SPCh. 11 - Prob. 11.44SPCh. 11 - Both cis- and trans-2-methylcyclohexanol undergo...Ch. 11 - Prob. 11.46SPCh. 11 - Prob. 11.47SPCh. 11 - Show how you would make each compound, beginning...Ch. 11 - Predict the major products (including...Ch. 11 - Show how you would use simple chemical tests to...Ch. 11 - The compound shown below has three different types...Ch. 11 - Prob. 11.52SPCh. 11 - Prob. 11.53SPCh. 11 - Prob. 11.54SPCh. 11 - Prob. 11.55SPCh. 11 - Show how you would synthesize the following...Ch. 11 - Show how you would synthesize the following...Ch. 11 - The following pseudo-syntheses (guaranteed not to...Ch. 11 - Two unknowns, X and Y, both having the molecular...Ch. 11 - The Williamson ether synthesis involves the...Ch. 11 - Prob. 11.61SPCh. 11 - Prob. 11.62SPCh. 11 - Alcohols combine with ketones and aldehydes to...Ch. 11 - Prob. 11.64SPCh. 11 - Prob. 11.65SPCh. 11 - Prob. 11.66SP
Knowledge Booster
Similar questions
- Determine the structure of the methyl ester and organomagnesium bromide reagents that can be combined to form the following alcohol: Part 1: Draw the bond-line formula for the methyl ester reagent. Disregard stereochemistry. Part 2: Draw the bond-line formula for the organomagnesium bromide reagent. Disregard stereochemistry.arrow_forwardWhen propene reacts with gaseous hydrogen bromide, HBr, two products, 1-bromopropane and 2-bromopropane are formed. The reaction is a two-step process in which the electrophilic attack occurs in the first step. Identify the electrophile in this reaction Draw a diagram showing the first step of the reaction that leads to the production of 2-bromopropane.arrow_forward10) Synthesis: Make the following products from a suitable cyclic alkene starting material. Look at the functional group PATTERN present in the molecule, including stereochemistry. ♡ Br Brarrow_forward
- Butene (CH2CHCH2CH3) reacts with hydrogen chloride (HCl) at room temperature. Draw the displayed formulae of the products formed in this reaction. State the name of the above reaction mechanism. Alkene Propene reacts with hydrogen bromide (HBr) at room temperature to produce, 1-bromopropane and 2-bromopropane. H2C=CHCH3 + HBr → CH2(Br)CH2CH3 + CH3CH(Br)CH3 Draw out the reaction mechanism of the reaction between propene and hydrogen bromide to produce 2-bromopropane. Use curly arrows to show the movement of electrons. The description should be detailed and must include the type of bond fission that takes place. You may sketch and insert suitable diagrams to aid your description if you wish. Referring to the above mechanism, explain why two products…arrow_forwardShow how to convert ethylene to these compounds. (a) Ethane (b) Ethanol (c) Bromoethane (d) 2-Chloroethanol (e) 1,2-Dibromoethane (f) 1,2-Ethanediol (g) Chloroethanearrow_forwardEsterication is the reaction of a carboxylic acid (RCOOH) with an alcohol (R'OH) to form an ester (RCOOR') with loss of water. Equation [1] is an example of an intermolecular esterication reaction. Equation [2] is an example of an intramolecular esterication reaction; that is, the carboxylic acid and alcohol are contained in the same starting material, forming a cyclic ester as product. The equilibrium constants for both reactions are given. Explain why Keq is different for these two apparently similar reactions.arrow_forward
- Which compound is a tertiary alcohol that may not be oxidized by H2CrO4 or MnO2? Which compound is a secondary alcohol that may be oxidized to a ketone by MnO2? Which compound is an alcohol that may be oxidized to an aldehyde by PCC?arrow_forwardThe reaction of ozone with 2-butene leads to -10 formation of aldehyde + ketone 0 aldehyde + alcohol 0 two molecules of carboxylic acid 0arrow_forward2-chloropropane is a major product of the reaction of chlorine with propane under ultraviolet light. Write the mechanism for this reaction including the initiation step and the two propagation steps.arrow_forward
- Hydration 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_forwardPredict the alcohol products of the hydration, hydroboration, and dihydroxylation of alkenes.arrow_forwardWe have covered several oxidants that use a multi-valent atom (Cr, Cl, S, or I) as their active 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, before and after the oxidation of an alcohol to a ketone or aldehyde. How many bonds to oxygen does each atom have before and after the oxidation? (a) the I in the DMP reagent (b) the carbinol C in the alcohol that is oxidizedarrow_forward
arrow_back_ios
arrow_forward_ios
Recommended textbooks for you
Organic ChemistryChemistryISBN:9781305580350Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. FootePublisher:Cengage Learning
Introduction to General, Organic and BiochemistryChemistryISBN:9781285869759Author:Frederick A. Bettelheim, William H. Brown, Mary K. Campbell, Shawn O. Farrell, Omar TorresPublisher:Cengage Learning
Chemistry & Chemical ReactivityChemistryISBN:9781133949640Author:John C. Kotz, Paul M. Treichel, John Townsend, David TreichelPublisher:Cengage Learning
Chemistry & Chemical ReactivityChemistryISBN:9781337399074Author:John C. Kotz, Paul M. Treichel, John Townsend, David TreichelPublisher:Cengage Learning
Organic Chemistry
Chemistry
ISBN:9781305580350
Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Publisher:Cengage Learning
Introduction to General, Organic and Biochemistry
Chemistry
ISBN:9781285869759
Author:Frederick A. Bettelheim, William H. Brown, Mary K. Campbell, Shawn O. Farrell, Omar Torres
Publisher:Cengage Learning
Chemistry & Chemical Reactivity
Chemistry
ISBN:9781133949640
Author:John C. Kotz, Paul M. Treichel, John Townsend, David Treichel
Publisher:Cengage Learning
Chemistry & Chemical Reactivity
Chemistry
ISBN:9781337399074
Author:John C. Kotz, Paul M. Treichel, John Townsend, David Treichel
Publisher:Cengage Learning