Organic Chemistry
12th Edition
ISBN: 9781118875766
Author: T. W. Graham Solomons, Craig B. Fryhle, Scott A. Snyder
Publisher: WILEY
expand_more
expand_more
format_list_bulleted
Concept explainers
Videos
Textbook Question
Chapter 11, Problem 11PP
Practice Problem 11.11
An exception to what is stated above has to do with syntheses of unsymmetrical ethers in which one alkyl group is a tert-butyl group and the other group is primary. For example, this synthesis can be accomplished by adding tm-butyl alcohol to a mixture of the primary alcohol and
Give a likely mechanism for this reaction and explain why it is successful.
Expert Solution & Answer
Want to see the full answer?
Check out a sample textbook solution
Students have asked these similar questions
Using your reaction roadmap as a guide, show how to convert 1-butanol and ethanol into racemic 2-ethoxy-1-butanol. You must use 1-butanol and ethanol as the source of
all carbon atoms in the ether product.
(1)
(2)
(3)
OH
(4)
2-ethoxy-1-butanol
(racemic)
OH
Suggest reagents and experimental conditions for each step in this synthesis.
From the choices provided, suggest appropriate reagents for each step. More than one reagent may be necessary. Use the minimum number of steps possible. Enter your
answer as a letter, or a series of letters, in the order necessary to bring about the steps shown.
Reagents:
OH
(c) ethylene oxide
(a) (CH3)3CO¯K+, THF (d) H₂SO4, H₂O
(b) OsO4, H₂O2
Br
OH
+
(9) H₂ SO4 (anhydrous) Na, NH3 (1)
(k) NBS, heat
(e) m-chloroperoxybenzoic acid
(mCPBA)
(f) pyridinium chlorochromate) PBr3
(PCC)
(h) NaOH
(N-bromosuccinimide)
Previous
Next
(c)
(b)
10:43 M
-4-
21%
QUESTION 4
Propose the mechanism for each of the following reactions. Show all intermediates and
use the correct arrow formalism for the flow of electrons. Give all important resonance
structures. Do not use generic "R" groups in your examples.
[30]
(a) An example for the so called Darzens reaction is the base catalyzed reaction of ethylchloro
acetate with cyclohexanone to give the epoxy ester shown. The first step is a carbonyl
condensation reaction, and the second step is an SN2 reaction.
(5)
|||
Eto OEt
OEt
°
요
OH
-5-
1. NaOEt, EtOH
2. BrCH2(CH2)2CH2Br
3. H3O+, heat
OEt
NaOEt
HOEt
محمد
(8)
OH
(6)
Using your reaction roadmap as a guide, show how to convert 1-butanol and ethanol into racemic 2-ethoxy-1-butanol. You must use 1-butanol and ethanol as the source of
all carbon atoms in the ether product.
(1)
(2)
(3)
OH
(4)
2-ethoxy-1-butanol
(racemic)
OH
OH
Suggest reagents and experimental conditions for each step in this synthesis.
From the choices provided, suggest appropriate reagents for each step. More than one reagent may be necessary. Use the minimum number of steps possible. Enter your
answer as a letter, or a series of letters, in the order necessary to bring about the steps shown.
Reagents:
1
(a) (CH3)3 CO K+, THF (d) H₂SO4, H₂O
(b) OsO4, H₂O2
(c) ethylene oxide
Br
(e) m-chloroperoxybenzoic acid
OH
(mCPBA)
(f) pyridinium chlorochromate
(PCC)
|| Ⓡ
(g) H₂SO4 (anhydrous)
(h) NaOH
(i) PBr3
(j) Na, NH3 (1)
(k) NBS, heat
(N-bromosuccinimide)
Previous
Next
Chapter 11 Solutions
Organic Chemistry
Ch. 11 - Prob. 1PPCh. 11 - Practice Problem 11.2 Give bond-line formulas and...Ch. 11 - Prob. 3PPCh. 11 - Prob. 4PPCh. 11 - Prob. 5PPCh. 11 - Prob. 6PPCh. 11 - Prob. 7PPCh. 11 - Practice Problem 11.8 Show how you would prepare...Ch. 11 - Prob. 9PPCh. 11 - Prob. 10PP
Ch. 11 - Practice Problem 11.11
An exception to what is...Ch. 11 - Prob. 12PPCh. 11 - Prob. 13PPCh. 11 - Prob. 14PPCh. 11 - Prob. 15PPCh. 11 - Prob. 16PPCh. 11 - Prob. 17PPCh. 11 - Prob. 18PPCh. 11 - Practice Problem 11.19
Propose structures for each...Ch. 11 - Prob. 20PPCh. 11 - Prob. 21PPCh. 11 - Prob. 22PPCh. 11 - Prob. 23PPCh. 11 - Prob. 24PPCh. 11 - Give an IUPAC substitutive name for each of the...Ch. 11 - Prob. 26PCh. 11 - Prob. 27PCh. 11 - Prob. 28PCh. 11 - Prob. 29PCh. 11 - 11.30. Show how you might prepare 2-bromobutane...Ch. 11 - Prob. 31PCh. 11 - Prob. 32PCh. 11 - Prob. 33PCh. 11 - Considering A-L to represent the major products...Ch. 11 - Write structures for the products that would be...Ch. 11 - Prob. 36PCh. 11 - Provide the reagents necessary for the following...Ch. 11 - 11.38. Predict the major product from each of the...Ch. 11 - Predict the products from each of the following...Ch. 11 - Provide the reagents necessary to accomplish the...Ch. 11 - 11.41. Provide reagents that would accomplish the...Ch. 11 - Prob. 42PCh. 11 - 11.43. A synthesis of the -receptor blocker called...Ch. 11 - Prob. 44PCh. 11 - Prob. 45PCh. 11 - 11.46. For each of the following, write a...Ch. 11 - 11.47. Vicinal halo alcohols (halohydrins) can be...Ch. 11 - Prob. 48PCh. 11 - Prob. 49PCh. 11 - Prob. 50PCh. 11 - Prob. 51PCh. 11 - Prob. 52PCh. 11 - Outlined below is a synthesis of the gypsy moth...Ch. 11 - Prob. 54PCh. 11 - Prob. 55PCh. 11 - Prob. 56PCh. 11 - 11.57. When the 3-bromo-2-butanol with the...Ch. 11 - 11.58. Reaction of an alcohol with thionyl...Ch. 11 - Prob. 59PCh. 11 - Prob. 60PCh. 11 - Prob. 1LGPCh. 11 - Prob. 2LGPCh. 11 - Synthesize the compound shown below from...
Additional Science Textbook Solutions
Find more solutions based on key concepts
Q2. This image represents a particulate view of a sample of matter. Classify the sample according to its compos...
Chemistry: A Molecular Approach (4th Edition)
Compare each of the mechanisms listed here with the mechanism for each of the two parts of the acid-catalyzed h...
Organic Chemistry (8th Edition)
Why can algae and cyanobacteria be considered indicators of productivity as well as of pollution?
Laboratory Experiments in Microbiology (12th Edition) (What's New in Microbiology)
Use the key to classify each of the following described tissue types into one of the four major tissue categori...
Anatomy & Physiology (6th Edition)
Two culture media were inoculated with four different bacteria. After incubation, the following results were ob...
Microbiology: An Introduction
The term isomers must be explained. Concept Introduction : Isomers are compounds with same molecular formula bu...
Living By Chemistry: First Edition Textbook
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
- we know that ethers, such as diethyl ether and tetrahydrofuran, are quite resistant to the action of dilute acids and require hot concentrated HI or HBr for cleavage. However, acetals in which two ether groups are linked to the same carbon undergo hydrolysis readily, even in dilute aqueous acid. How do you account for this marked difference in chemical reactivity toward dilute aqueous acid between ethers and acetals?arrow_forwardSubject-chemistryarrow_forward9. Plan syntheses of the following compounds. You may use the given starting material and any compound containing three or fewer carbons. (a) (b) (c) (d) by Br or Br H Br H OH = OHarrow_forward
- The following sequence of steps converts (R)-2-octanol to (S)-2-octanol. Propose structural formulas for intermediates A and B, specify the configuration of each, and account for the inversion of configuration in this sequence.arrow_forward7. The following reaction is from a synthesis of the natural product salinipyrone A. After being synthesized, salinipyrone A was then screened for antitumor activity. Predict the major product of this reaction. Note that the TBS-protected alcohol is stable to the Wittig reaction condition --1 الله OTBS Me OTBS - 1-0-4-1-84 Si-t-Bu Me H Ph₂P=CHCO₂Etarrow_forward2B Suggest a short synthetic route for the preparation of compound D from compound C OH Br COOH C D Note: Apart from compound C, you can also use organic reagents with up to 1 C atom. The number of arrows in the figure above does not necessarily correspond to the number of steps.arrow_forward
- Please show me how to disconnect the first moleculearrow_forwardUsing your reaction roadmap as a guide, show how to convert cyclohexanol into racemic trans-1,2-cyclohexanediol. (1) (2) OH aa OH (3) trans-1,2-cyclohexanediol (racemic) OH "ОН Suggest reagents and experimental conditions for each step in this synthesis. From the choices provided, suggest appropriate reagents for each step. More than one reagent may be necessary. Use the minimum number of steps possible. Enter your answer as a letter, or a series of letters, in the order necessary to bring about the steps shown. Reagents: (c) ethylene oxide 1 OH (a) CH3ONa+, CH, OH (d) H₂SO4, H₂O (b) OsO4, H₂O2 ||Ⓡ (9) H₂SO4 (anhydrou$)) Na, NH3 (1) (k) NBS, heat (e) m-chloroperoxybenzoic acid (mCPBA) (f) pyridinium chlorochromatę) PBr3 (PCC) (h) NaOH (N-bromosuccinimide)arrow_forward6A2: Recognize and apply the general motif of electrophilic addition via the AE the mechanistic step, including matters of regiochemistry (Markovnikov's rule) and configuration/stereochemistry (AN with a carbocation vs. syn addition) to solve synthetic problems and predict products. Add all lone pairs and provide a detailed, electron-pushing mechanism for the reaction by following the mechanistic step descriptors. You must redraw the entire sequence (that is, not just draw over the given structures) to pass this problem. HO H. .H HO TRE- + HOH H AE 1,2R OH + HOH PT + H30Ⓡ C Garrow_forward
- I understand what reagents and or solvents can be used to get from an alkene to an alkyne but if someone could please show me step by step how each is used to perform the actual synthesis? Like how does each thing work to get to the next portion of the synthesis. I am truly struggling. thank youarrow_forward(b) Provide retrosynthetic steps leading to ketone 9 from bicyclic compound 8. Provide all intermediates (synthons) and their equivalents clearly labelled. No synthetic steps and mechanisms are required. | NC. 8arrow_forward3. An alcohol containing natural product A (C10H200) that is a common ingredient in cough drops yields two structurally isomeric alkenes, 1 and 2, on dehydration. Ozonolysis followed by an oxidative workup or a reductive workup as shown yields 3 and 4 from 1 and 2, respectively. Hydroboration of alkene 1 yields the starting alcohol A as the major product from 1. Hydroboration yields a mixture of the starting alcohol A and a diastereomer of A starting from alkene 2. Given this information deduce the structure of A, 1, and 2. Show the correct absolute and relative stereochemistry for A (the alcohol group is cis to a methyl group), 1, and 2 and correctly name these three compounds. H2SO4 heat 1) O3 Н. 1 (C10H18) 2. Zn, H3O* 3 H. A (C10H200) H2SO4 1) O3 н СНО heat 2 (C10H18) 2. Zn, H3O* Н 4arrow_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 Learning
Organic Chemistry
Chemistry
ISBN:9781305580350
Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Publisher:Cengage Learning
Alcohols, Ethers, and Epoxides: Crash Course Organic Chemistry #24; Author: Crash Course;https://www.youtube.com/watch?v=j04zMFwDeDU;License: Standard YouTube License, CC-BY