Organic Chemistry
8th Edition
ISBN: 9781305580350
Author: William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Publisher: Cengage Learning
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Chapter 11, Problem 11.19P
Interpretation Introduction
Interpretation:
Synthesis of triethanolamine from ethylene oxide has to be proposed.
Concept introduction:
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(a) Explain how NaBH, in CH;OH can reduce hemiacetal A to 1,4-butanediol (HOCH,CH,CH,CH,OH). (b) What product is
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Arrange the following compounds in the increasing order of their acid strength: p-cresol, p-nitrophenol, phenol
(a) Tsomane and Nyiko were given a task of synthesising methylenecyclohexane
2. After a brief discussion with each other, Tsomane proposed Method A to
synthesise 2 from cyclohexanone 1 while Nyiko proposed Method B that
started from hydroxymethylcyclohexane 3. Each student believed that their
proposed method is better than the other. (Scheme below)
(ii)
Ph
Ph
Ph
640
THF
A
1
B
H₂SO4
100 °C
3
OH
In analysing both these methods, are there other possible alkene
products other than methylenecyclohexane 2?
Chapter 11 Solutions
Organic Chemistry
Ch. 11.2 - Write IUPAC and common names for these ethers. (a)...Ch. 11.3 - Arrange these compounds in order of increasing...Ch. 11.4 - Show how you might use the Williamson ether...Ch. 11.4 - Show how ethyl hexyl ether might be prepared by a...Ch. 11.5 - Account for the fact that treatment of tert-butyl...Ch. 11.5 - Draw structural formulas for the major products of...Ch. 11.6 - Prob. 11.7PCh. 11.8 - Draw the expected products of Sharpless...Ch. 11.9 - Prob. AQCh. 11.9 - Prob. BQ
Ch. 11.9 - Prob. CQCh. 11.9 - Prob. DQCh. 11 - Write names for these compounds. Where possible,...Ch. 11 - Prob. 11.11PCh. 11 - Each compound given in this problem is a common...Ch. 11 - Account for the fact that tetrahydrofuran (THF) is...Ch. 11 - Prob. 11.14PCh. 11 - Write equations to show a combination of reactants...Ch. 11 - Propose a mechanism for this reaction.Ch. 11 - Prob. 11.17PCh. 11 - Prob. 11.18PCh. 11 - Prob. 11.19PCh. 11 - Prob. 11.20PCh. 11 - Ethylene oxide is the starting material for the...Ch. 11 - Prob. 11.22PCh. 11 - Predict the structural formula of the major...Ch. 11 - The following equation shows the reaction of...Ch. 11 - Propose a mechanism to account for this...Ch. 11 - Acid-catalyzed hydrolysis of the following epoxide...Ch. 11 - Prob. 11.27PCh. 11 - Prob. 11.28PCh. 11 - Prob. 11.29PCh. 11 - Propose a mechanism for the following...Ch. 11 - Show reagents and experimental conditions to...Ch. 11 - Starting with cis-3-hexene, show how to prepare...Ch. 11 - Show reagents to convert cycloheptene to each of...Ch. 11 - Show reagents to convert bromocyclopentane to each...Ch. 11 - Prob. 11.35PCh. 11 - Starting with acetylene and ethylene oxide as the...Ch. 11 - Following are the steps in the industrial...Ch. 11 - Prob. 11.38PCh. 11 - Prob. 11.39PCh. 11 - Aldehydes and ketones react with one molecule of...Ch. 11 - Prob. 11.42PCh. 11 - Write the products of the following sequences of...Ch. 11 - Using your reaction roadmap as a guide, show how...Ch. 11 - Using your reaction roadmap as a guide, show how...Ch. 11 - Using your reaction roadmap as a guide, show how...Ch. 11 - During the synthesis of the antiasthmatic drug...Ch. 11 - Prob. 11.48P
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- (a) Tsomane and Nyiko were given a task of synthesising methylenecyclohexane 2. After a brief discussion with each other, Tsomane proposed Method A to synthesise 2 from cyclohexanone 1 while Nyiko proposed Method B that started from hydroxymethylcyclohexane 3. Each student believed that their proposed method is better than the other. (Scheme below) (1) Ph Ph 836 Ph THF A 1 B H₂SO4 100 °C 3 OH Which of the two methods (A or B) is more likely give high yield of methylenecyclohexane 2? Briefly explain.arrow_forwardPrepare the following compound by the synthesis of malonic acidarrow_forward9arrow_forward
- 1. Write the equilibrium-constant expressions and obtain numerical values for each constant in(a) the basic dissociation of aniline, C6H5NH2 .(b) the acidic dissociation of hypochlorous acid, HClO.(c) the acidic dissociation of methyl ammonium hydrochloride, CH3NH3Cl.(d) the basic dissociation of NaNO2 .(e) the dissociation of H3AsO3 to H3O + and AsO33- 2. The chemicals A and B react as follows to produce C and D: A + B ↔ C + DKe = [C] [D] [A] [B] The equilibrium constant Ke has a value of 0.30. Assume 0.20 mol of A and 0.50 mol of B are dissolved in 1.00 L, and the reaction proceeds. Calculate the concentrations of reactants [A], [B] and products [C], [D] at equilibrium. Using step-by-step processarrow_forwardSuggest a possible structure for Compound X.arrow_forward3. Provide the products, intermediates, and/or reagents for the following reactions: (a) CH3 (i) H2N CH3 pyridine Ph (b) он PBr3 PPh, кови (ii) (iii) (iv) then (c) Ph Br. (v) CH3 (d) HNO, (excess) (vi) CH3 H2SO4 (e) 2 Li(s) Ph-CEN (vii) (viii) then HCI, H20 HO (x) (1) DIBAL-H HO t-Bu, (ix) then NaOH, H20 p-TSOH (g) NH2 CH3 (xi) Но pyridine Ноarrow_forward
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