Organic Chemistry (9th Edition)
9th Edition
ISBN: 9780321971371
Author: Leroy G. Wade, Jan W. Simek
Publisher: PEARSON
expand_more
expand_more
format_list_bulleted
Concept explainers
Videos
Textbook Question
Chapter 26.7C, Problem 26.16P
- a. Propose a mechanism for the reaction of bisphenol A with phosgene.
- b. Diethyl carbonate serves as a less-toxic alternative to phosgene for making Lexan. Propose a mechanism for the transesterification of diethyl carbonate with bisphenol A, catalyzed by a trace of sodium ethoxide. What small molecule is given off in this - condensation?
Expert Solution & Answer
Want to see the full answer?
Check out a sample textbook solution
Students have asked these similar questions
Propose a mechanism for the conjugate addition of a nucleophile ( Nuc:" ) to acrylonitrile (
CH,=CHCN ). Use resonance forms to show how the cyano group activates the double
bond for conjugate addition.
What is the best set of reagents to achieve deoxygenation of 2-pentanone to pentane?
A. NaClO2/NaH2PO4
B. LiAlH4, Et2O
C. DIBAL-H, THF
D. NH2NH2/t-BuOK, DMSO
Show how propanolol can be synthesized from 1-naphthol, epichlorohydrin , and isopropylamine.
Chapter 26 Solutions
Organic Chemistry (9th Edition)
Ch. 26.2A - Show the intermediate that would result if the...Ch. 26.2A - Prob. 26.2PCh. 26.2A - Prob. 26.3PCh. 26.2B - Prob. 26.4PCh. 26.2B - Prob. 26.5PCh. 26.2B - Chain branching occurs in cationic polymerization...Ch. 26.2C - Prob. 26.7PCh. 26.2C - Prob. 26.8PCh. 26.2C - Chain branching is not as common with anionic...Ch. 26.3 - Prob. 26.10P
Ch. 26.5 - Prob. 26.11PCh. 26.6 - Prob. 26.12PCh. 26.7A - Prob. 26.13PCh. 26.7B - Prob. 26.14PCh. 26.7B - Prob. 26.15PCh. 26.7C - a. Propose a mechanism for the reaction of...Ch. 26.7C - Prob. 26.17PCh. 26.7D - Prob. 26.18PCh. 26.7D - Prob. 26.19PCh. 26.7D - Prob. 26.20PCh. 26 - Prob. 26.21SPCh. 26 - Prob. 26.22SPCh. 26 - Poly(trimethylene carbamate) is used in...Ch. 26 - Prob. 26.24SPCh. 26 - Urylon fibers are used in premium fishing nets...Ch. 26 - Prob. 26.26SPCh. 26 - Prob. 26.27SPCh. 26 - Polyoxymethylene (polyformaldehyde) is the tough,...Ch. 26 - Prob. 26.29SPCh. 26 - Prob. 26.30SPCh. 26 - Prob. 26.31SPCh. 26 - Prob. 26.32SPCh. 26 - Prob. 26.33SPCh. 26 - Prob. 26.34SPCh. 26 - The polyester named Lactomer is an alternating...Ch. 26 - Prob. 26.36SP
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
- Following is a synthesis for toremifene, a nonsteroidal estrogen antagonist whose structure is closely related to that of tamoxifen. (a) This synthesis makes use of two blocking groups, the benzyl (Bn) group and the tetrahydropyranyl (THP) group. Draw a structural formula of each group and describe the experimental conditions under which it is attached and removed. (b) Discuss the chemical logic behind the use of each blocking group in this synthesis. (c) Propose a mechanism for the conversion of D to E. (d) Propose a mechanism for the conversion of F to toremifene. (e) Is toremifene chiral? If so, which of the possible stereoisomers are formed in this synthesis?arrow_forwardWhen warmed in dilute sulfuric acid, 1-phenyl-1,2-propanediol undergoes dehydration and rearrangement to give 2-phenylpropanal. (a) Propose a mechanism for this example of a pinacol rearrangement (Section 10.7). (b) Account for the fact that 2-phenylpropanal is formed rather than its constitutional isomer, 1-phenyl-1-propanone.arrow_forwardWittig reactions with the following -chloroethers can be used for the synthesis of aldehydes and ketones. (a) Draw the structure of the triphenylphosphonium salt and Wittig reagent formed from each chloroether. (b) Draw the structural formula of the product formed by treating each Wittig reagent with cyclopentanone. Note that the functional group is an enol ether or, alternatively, a vinyl ether. (c) Draw the structural formula of the product formed on acid-catalyzed hydrolysis of each enol ether from part (b).arrow_forward
- Show how to bring about each step in this synthesis of the herbicide propranil.arrow_forwardPropose a mechanism to account for the formation of 3, 5-dimethyl- pyrazole from hydrazine and 2, 4-pentanedione. Look carefully to see what has happened to each carbonyl carbon in going from starting material to product.arrow_forwardHow would you prepare the following compounds from 2- phenylethanol? More than one step may be required. a. Styrene (PhCH=CH2) b. Phenylacetaldehyde (PhCH2CHO) c. Phenylacetic acid (PhCH2CO2H) d. Benzoic acid e. Ethylbenzene f. Benzaldehyde g. 1-Phenylethanol h. 1-Bromo-2-phenylethanearrow_forward
- Which of the following starting materials and reagents would be best to produce 2-hexanol? a. heptanal and 1. CH3MgBr 2. H3O* b. pentanal and 1. CH3MgBr, 2. H30* c. hexanal and 1. CH3MgBr, 2. H30* d. butanal and 1. CH3CH2MgBr, 2. H3O*arrow_forwardShow how the reagent for Step 6 can be prepared from salicylic acid (2-hydroxybenzoic acid). Salicylic acid, the starting material for the synthesis of aspirin and a number of other pharmaceuticals, is readily available by the Kolbe carboxylation of phenolarrow_forwardH3C OH 1. Br2, PBг3 2. H₂O H3C OH Br The a-bromination of carbonyl compounds by Br₂ in acetic acid is limited to aldehydes and ketones because acids, esters, and amides don't enolize to a sufficient extent. Carboxylic acids, however, can be a-brominated by first converting the carboxylic acid to an acid bromide by treatment with PBr3. Following enolization of the acid bromide, Br2 reacts in an a-substitution reaction. Hydrolysis of the acid bromide completes the reaction. Draw curved arrows to show the movement of electrons in this step of the mechanism. Arrow-pushing Instructions Br Br зь P-Br Br H₂C H₂C SH Br Brarrow_forward
- From the table of available reagents select the one(s) you would use to convert cyclohexanone to the following compound: CH,CH,CO,H Use the minimum number of steps; from one to five are required. List reagents by letter in the order that they are used; example: fa. Reagents Available a. BH3, THF; followed by H₂O₂, OH b. Br₂, CH3CO₂H c. HCN, KCN d. H3O*, heat e. LDA (lithium diisopropylamide) f. NaBH4 g. Na* -CH(CO₂C₂H5) (from CH₂(CO₂C₂H5)2 + Na* -OC₂H5) h. PBr3 i. PhCH₂Br j. Ph3P+--CH₂ k. pyridine, heat I. PhBrarrow_forwardIdentify products A and B from the given 1H NMR data.a. Treatment of CH2 = CHCOCH3 with one equivalent of HCl forms compound A. A exhibits the following absorptions in its 1H NMR spectrum: 2.2 (singlet, 3 H), 3.05 (triplet, 2 H), and 3.6 (triplet, 2 H) ppm. What is the structure of A?b. Treatment of acetone [(CH3)2C = O] with dilute aqueous base forms B. Compound B exhibits four singlets in its 1H NMR spectrum at 1.3 (6 H), 2.2 (3 H), 2.5 (2 H), and 3.8 (1 H) ppm. What is the structure of B?arrow_forwardIdentify products A and B from the given 1H NMR data. a.Treatment of CH2=CHCOCH3 with one equivalent of HCl forms compound A. A exhibits the following absorptions in its 1H NMR spectrum: 2.2 (singlet, 3 H), 3.05 (triplet, 2 H), and 3.6 (triplet, 2 H) ppm. What is the structure of A? b.Treatment of acetone [(CH3)2C=O] with dilute aqueous base forms B. Compound B exhibits four singlets in its 1H NMR spectrum at 1.3 (6 H), 2.2 (3 H), 2.5 (2 H), and 3.8 (1 H) ppm. What is the structure of B?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 Learning
Organic Chemistry
Chemistry
ISBN:9781305580350
Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Publisher:Cengage Learning
Coenzymes and cofactors; Author: CH15 SWAYAM Prabha IIT Madras;https://www.youtube.com/watch?v=bubY2Nm7hVM;License: Standard YouTube License, CC-BY
Aromaticity and Huckel's Rule; Author: Professor Dave Explains;https://www.youtube.com/watch?v=7-BguH4_WBQ;License: Standard Youtube License