Organic Chemistry - Standalone book
10th Edition
ISBN: 9780073511214
Author: Francis A Carey Dr., Robert M. Giuliano
Publisher: McGraw-Hill Education
expand_more
expand_more
format_list_bulleted
Question
Chapter 17.11, Problem 13P
Interpretation Introduction
Interpretation:
The major organic product that is produced during the reaction of ethylene oxide with each of the following reagents is to be determined.
Concept Introduction:
>In comparison to simple ethers,
On reacting with anionic nucleophiles, epoxides form ring-opened products. This reaction is quite rapid and is exothermic in nature.
>The high reactivity of epoxides towards anionic nucleophiles is due to the presence of angle strain in epoxide and this is relieved by opening of the ring.
Expert Solution & Answer
Want to see the full answer?
Check out a sample textbook solutionStudents have asked these similar questions
Problem
19.22 Show how ethyl bromide can be used as a starting material in the preparation of each of the
following compounds. (Hint: How are Grignard reagents prepared?)
HO
`CH;CH3
(a)
OH
(b)
OH
(c) 1-butanol
(d)
PHCHCH,CH;
(CH;CH;),CCH3
17.36 Tamoxifen is an estrogen receptor modulator that is used in the treatment of breast cancer. Provide the missing reagents and the structure of compound A in the synthesis of tamoxifen. Page 707 HO (CH3)2N 1. C,H,MgBr 2. H + Compound A (CH3)2N Tamoxifen
Rank the following compounds in order of increasing acidity, and explain in detail your choice of order.
Chapter 17 Solutions
Organic Chemistry - Standalone book
Ch. 17.1 - Prob. 1PCh. 17.2 - The heats of combustion of 1, 2-epoxybutane...Ch. 17.3 - Prob. 3PCh. 17.4 - Prob. 4PCh. 17.5 - Prob. 5PCh. 17.6 - Problem 17.6 (a) Write equations describing two...Ch. 17.6 - Problem 17.7 Only one combination of alkyl halide...Ch. 17.6 - Prob. 8PCh. 17.8 - Prob. 9PCh. 17.8 - Prob. 10P
Ch. 17.9 - Prob. 11PCh. 17.10 - Problem 17.12 Classify the bromohydrins formed...Ch. 17.11 - Prob. 13PCh. 17.11 - Prob. 14PCh. 17.12 - Prob. 15PCh. 17.12 - Prob. 16PCh. 17.14 - Prob. 17PCh. 17.15 - Prob. 18PCh. 17.16 - Prob. 19PCh. 17.17 - Problem 17.20 There is another oxygen-stabilized...Ch. 17 - Prob. 21PCh. 17 - Many ethers, including diethyl ether, are...Ch. 17 - Although epoxides are always considered to have...Ch. 17 - The name of the parent six-membered...Ch. 17 - Prob. 25PCh. 17 - Prob. 26PCh. 17 - Prob. 27PCh. 17 - Prob. 28PCh. 17 - Prob. 29PCh. 17 - Given that: does the product of the analogous...Ch. 17 - Prob. 31PCh. 17 - Prob. 32PCh. 17 - Prob. 33PCh. 17 - Prob. 34PCh. 17 - Prob. 35PCh. 17 - Prob. 36PCh. 17 - When (R)-(+)-2-phenyl-2-butanol is allowed to...Ch. 17 - Prob. 38PCh. 17 - Prob. 39PCh. 17 - Write a mechanism for the following reaction.Ch. 17 - Prob. 41PCh. 17 - Prob. 42PCh. 17 - Prob. 43PCh. 17 - Prob. 44PCh. 17 - Prob. 45PCh. 17 - Prob. 46DSPCh. 17 - Prob. 47DSPCh. 17 - Prob. 48DSPCh. 17 - Prob. 49DSPCh. 17 - Epoxide Rearrangements and the NIH Shift This...Ch. 17 - Epoxide Rearrangements and the NIH Shift This...
Knowledge Booster
Similar questions
- 18.26 Predict the products of the following ether cleavage reactions: LOCH CH3 OC(CH3)3 (a) HI CF3CO,H, ? (b) H2O HI HI (c) Н,С— СНОСH,CH, (d) (CH3);CCH,OCH,CH3 H20 H2Oarrow_forwardArrange the following compounds in order of decreasing acidity and explain why?arrow_forwardOctinoxate is an unsaturated ester used as an active ingredient in sunscreens. (a) What carbonyl compounds are needed to synthesize this compound using a condensation reaction? (b) Devise a synthesis of octinoxate from the given organic starting materials and any other needed reagents.arrow_forward
- Arrange each group of compounds in order of increasing basicity.(a) CH3COO-, ClCH2COO-, and PhO- (b) sodium acetylide, sodium amide, and sodium acetate(c) sodium benzoate, sodium ethoxide, and sodium phenoxide (d) pyridine, sodium ethoxide, and sodium acetatearrow_forwardGive the structure of compound A.arrow_forwardCompound A has acidity stronger than compound Barrow_forward
- Arrange each group of compounds in order of increasing acidity.(c) benzoic acid, o-nitrobenzoic acid, m-nitrobenzoic acidarrow_forwardMeO 22.55 One potential synthesis of the anti-inflammatory and analgesic drug nabumetone is chloromethylation (Problem 22.48) of 2-methoxynaphthalene followed by an acetoacetic ester synthesis (Section 19.6). 5 3 6 CH₂O CI acetoacetic ester synthesis HC 7 MeO MeO 1 8 2-Methoxynaphthalene Nabumetone (a) Account for the regioselectivity of chloromethylation at carbon 6 rather than at carbon 5 or 7. (b) Show steps in the acetoacetic ester synthesis by which the synthesis of nabum- etone is completed.arrow_forward- Rank the following substances in order of increasing acidity: (a) Phenol, p-methylphenol, p-(trifluoromethyl)phenol (b) Benzyl alcohol, phenol, p-hydroxybenzoic acidarrow_forward
- 18.26 Synthesize each of the following compounds from diethyl malonate or ethyl acetoacetate and any other organic and inorganic reagents. (a) (c) (e) OH (b) OH (d) (f)arrow_forwardPropose a reasonable synthesis of the following reaction:.arrow_forwardLinalool and lavandulol are two of the major components of lavender oil. (a) What organolithium reagent and carbonyl compound can be used to make each alcohol? (b) How might lavandulol be formed by reduction of a carbonyl compound? (c) Why can't linalool be prepared by a similar pathway?arrow_forward
arrow_back_ios
SEE MORE QUESTIONS
arrow_forward_ios
Recommended textbooks for you
- ChemistryChemistryISBN:9781305957404Author:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCostePublisher:Cengage LearningChemistryChemistryISBN:9781259911156Author:Raymond Chang Dr., Jason Overby ProfessorPublisher:McGraw-Hill EducationPrinciples of Instrumental AnalysisChemistryISBN:9781305577213Author:Douglas A. Skoog, F. James Holler, Stanley R. CrouchPublisher:Cengage Learning
- Organic ChemistryChemistryISBN:9780078021558Author:Janice Gorzynski Smith Dr.Publisher:McGraw-Hill EducationChemistry: Principles and ReactionsChemistryISBN:9781305079373Author:William L. Masterton, Cecile N. HurleyPublisher:Cengage LearningElementary Principles of Chemical Processes, Bind...ChemistryISBN:9781118431221Author:Richard M. Felder, Ronald W. Rousseau, Lisa G. BullardPublisher:WILEY
Chemistry
Chemistry
ISBN:9781305957404
Author:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Publisher:Cengage Learning
Chemistry
Chemistry
ISBN:9781259911156
Author:Raymond Chang Dr., Jason Overby Professor
Publisher:McGraw-Hill Education
Principles of Instrumental Analysis
Chemistry
ISBN:9781305577213
Author:Douglas A. Skoog, F. James Holler, Stanley R. Crouch
Publisher:Cengage Learning
Organic Chemistry
Chemistry
ISBN:9780078021558
Author:Janice Gorzynski Smith Dr.
Publisher:McGraw-Hill Education
Chemistry: Principles and Reactions
Chemistry
ISBN:9781305079373
Author:William L. Masterton, Cecile N. Hurley
Publisher:Cengage Learning
Elementary Principles of Chemical Processes, Bind...
Chemistry
ISBN:9781118431221
Author:Richard M. Felder, Ronald W. Rousseau, Lisa G. Bullard
Publisher:WILEY