ORGANIC CHEMISTRY(LL)-W/SG.+SOLN+ACCESS
8th Edition
ISBN: 9780134649818
Author: Bruice
Publisher: PEARSON
expand_more
expand_more
format_list_bulleted
Concept explainers
Question
Chapter 15, Problem 65P
Interpretation Introduction
Interpretation:
The role of
Concept introduction:
Transesterification is the process of formation of a new ester molecule from the reaction of alcohol and an ester. This is like hydrolysis of ester but here nucleophile is alcohol molecule instead of
Expert Solution & Answer
Want to see the full answer?
Check out a sample textbook solutionStudents have asked these similar questions
A) Considering compounds 2a through 2l, identify:
1)one pair of geometric isomers
2)two pairs of enantiomers and
3)three pairs of identical molecules
B) Give the names, including the configurations, of each of the geometric isomers and of each of the enantiomers identified in 1A and 1B. Draw the relevant structures.
C) Sort compounds 2a, 2b, 2c, 2f and 2k in order of increasing solubility in water and briefly justify.
A difficult problem in the synthesis of PGF2α is the introduction of the OH group at C15 in the desired configuration.
a. Label this stereogenic center as R or S.
b. A well known synthesis of PGF2α involves reaction of A with Zn(BH4)2, a metal hydride reagent similar in reactivity to NaBH4, to form two isomeric products, B and C. Draw their structures and indicate their stereochemical relationship.
c. Suggest a reagent to convert A to the single stereoisomer X.
A difficult problem in the synthesis of PGF2α is the introduction of the OH group at C15 in the desired configuration. a. Label this stereogenic center as R or S. b. A well-known synthesis of PGF2α involves reaction of A with Zn(BH4)2, a metal hydride reagent similar in reactivity to NaBH4, to form two isomeric products, B and C. Draw their structures and indicate their stereochemical relationship. d. Suggest a reagent to convert A to the single stereoisomer X.
Chapter 15 Solutions
ORGANIC CHEMISTRY(LL)-W/SG.+SOLN+ACCESS
Ch. 15.1 - The aromas of many flowers and fruits are due to...Ch. 15.1 - Name the following:Ch. 15.1 - Prob. 3PCh. 15.2 - Which is longer, the carbon-oxygen single bond in...Ch. 15.2 - There are three carbon-oxygen bonds in methyl...Ch. 15.2 - Prob. 6PCh. 15.4 - a. What is the product of the reaction of acetyl...Ch. 15.4 - What is the product of an acyl substitution...Ch. 15.5 - a. Which compound has the stretching vibration for...Ch. 15.5 - Using the pKa values listed in Table 15.1, predict...
Ch. 15.5 - Is the following statement true or false? If the...Ch. 15.6 - Starting with acetyl chloride, what neutral...Ch. 15.6 - Prob. 13PCh. 15.7 - Starting with methyl acetate, what neutral...Ch. 15.7 - We saw that it is necessary to use excess amine in...Ch. 15.7 - Prob. 17PCh. 15.7 - Which ester hydrolyzes more rapidly? a. methyl...Ch. 15.7 - a. state three factors that cause the uncatalyzed...Ch. 15.8 - Prob. 21PCh. 15.8 - Using the mechanism for the acid-catalyzed...Ch. 15.8 - Prob. 23PCh. 15.8 - Show the mechanism for the acid-catalyzed...Ch. 15.8 - Prob. 25PCh. 15.8 - Write the mechanism for the acid-catalyzed...Ch. 15.8 - Write the mechanism for the acid-catalyzed...Ch. 15.9 - Prob. 28PCh. 15.9 - Prob. 29PCh. 15.10 - Show how each of the following esters could he...Ch. 15.10 - Prob. 32PCh. 15.11 - Prob. 33PCh. 15.11 - Which of the following reactions leads to the...Ch. 15.12 - Prob. 35PCh. 15.12 - Prob. 36PCh. 15.13 - Prob. 37PCh. 15.14 - Prob. 38PCh. 15.14 - Prob. 39PCh. 15.15 - Prob. 40PCh. 15.15 - Which alkyl halides from the carboxylic acids...Ch. 15.16 - Prob. 43PCh. 15.16 - Prob. 44PCh. 15.16 - Prob. 45PCh. 15.17 - Prob. 46PCh. 15.18 - How could you synthesize the following compounds...Ch. 15 - Prob. 48PCh. 15 - Name the following:Ch. 15 - Prob. 50PCh. 15 - What compound are obtained from the fallowing...Ch. 15 - a. Rank the following esters in order of...Ch. 15 - Because bromocyclohexane is a secondary alkyl...Ch. 15 - a. Which compound would you expect to have a...Ch. 15 - How could you use 1H NMR spectroscopy to...Ch. 15 - Rank the following compounds in order of...Ch. 15 - Prob. 57PCh. 15 - Prob. 58PCh. 15 - Prob. 59PCh. 15 - A compound with molecular formula C5H10O2 gives...Ch. 15 - Prob. 61PCh. 15 - Prob. 62PCh. 15 - Prob. 63PCh. 15 - Prob. 64PCh. 15 - Prob. 65PCh. 15 - Prob. 66PCh. 15 - Two products, A and B, are obtained from the...Ch. 15 - Prob. 68PCh. 15 - Prob. 69PCh. 15 - Prob. 70PCh. 15 - Prob. 71PCh. 15 - Prob. 72PCh. 15 - When treated with an equivalent of methanol,...Ch. 15 - a. Identify the two products obtained from the...Ch. 15 - Prob. 75PCh. 15 - Prob. 76PCh. 15 - a. When a carboxylic acid is dissolved in...Ch. 15 - Prob. 78PCh. 15 - Identity the major and minor products of the...Ch. 15 - When a compound with molecular formula C11H14O2...Ch. 15 - Prob. 81PCh. 15 - Prob. 82PCh. 15 - Prob. 83PCh. 15 - The 1H NMR spectra for two esters with molecular...Ch. 15 - Show how the following compounds could be prepared...Ch. 15 - Prob. 86PCh. 15 - Prob. 87PCh. 15 - The intermediate shown here is formed during the...Ch. 15 - Prob. 89PCh. 15 - Propose a mechanism that accounts for the...Ch. 15 - Catalytic antibodies catalyze a reaction by...Ch. 15 - Prob. 92P
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
- Aspirin, or 2-acetoxybenzoic acid, (C9H8O4) is often synthesised from salicylic acid.(i) Sketch and discuss any changes in the number of possible structural conformations ofaspirin relative to those of salicylic acid. (ii) Re-draw the structure predicted to be the lowest energy conformation of aspirin,indicating any expected stabilising and destabilising interactions. Justify your choice.arrow_forwardA chiral amine A having the R conguration undergoes Hofmann elimination to form an alkene B as the major product. B is oxidatively cleaved with ozone, followed by CH3SCH3, to form CH2 = O and CH3CH2CH2CHO. What are the structures of A and B?arrow_forwardWhen pure (S)-lactic acid is esterified by racemic butan-2-ol, the product is 2-butyl lactate, with the following structure:H+CH3 CH COOH CH3 CH CH3 CH CHOH OHCH2CH3 CH2CH3lactic acidC OOH CH O 3butan-2-ol 2-butyl lactate+(a) Draw three-dimensional structures of the two stereoisomers formed, specifying the configuration at each asymmetriccarbon atom. (Using your models may be helpful.)(b) Determine the relationship between the two stereoisomers you have drawnarrow_forward
- A difficult problem in the synthesis of PGF2α is the introduction of the OH group at C15 in the desired conguration.a. Label this stereogenic center as R or S.b. A well known synthesis of PGF2α involves reaction of A with Zn(BH4)2, a metal hydride reagent similar in reactivity to NaBH4, to form two isomeric products, B and C. Draw their structures and indicate their stereochemical relationship.c. Suggest a reagent to convert A to the single stereoisomer X.arrow_forwardplease provide the machanisms of 1a, 1e, 1farrow_forwardγ-Butyrolactone (C4H6O2, GBL) is a biologically inactive compound that is converted to the biologically active recreational drug GHB (Section 19.5) by a lactonase enzyme in the body. Since γ-butyrolactone is more fat soluble than GHB, it is more readily absorbed by tissues and thus produces a faster onset of physiological symptoms. γ-Butyrolactone shows an absorption in its IR spectrum at 1770 cm−1 and the following 1H NMR spectral data: 2.28 (multiplet, 2 H), 2.48 (triplet, 2 H), and 4.35 (triplet, 2 H) ppm. What is the structure of γ-butyrolactone?arrow_forward
- A chemist finds that the addition of (+)@epinephrine to the catalytic reduction of butan2-one gives a product that is slightly optically active, with a specific rotation of +0.45°. Calculate the percentages of (+)@butan@2@ol and (-)@butan@2@ol formed in this reaction.arrow_forward4 Show how the compound thiodiazine~C21H26N2S2~decomposes anaerobically and how these end products in turn decompose aerobically to stabilized sulfur and nitrogen compounds.arrow_forwardz When (R)-2-butanol is left standing in aqueous acid, it slowly loses its optical activity. Account for this observationarrow_forward
- Compound A, C5H10O, is one of the basic building blocks of nature. All steroids ans many other naturally occurring compounds are built from compound A. Spectroscopic analysis of A yields the following information. a) how many double bonds and/or rings does A have? b) From the IR spectrum, what is the identity of the oxygen-conataining functional group? c) what kinds of protons are responsible for the NMR absorptions listed d) propose a structure for Aarrow_forwardBenzene is one of the compounds used as octane enhancers in unleaded gasoline. It is manufactured by thecatalytic conversion of acetylene to benzene: 3C2 H2(g) ⇌ C6 H6(g). Which value of Kc would make this reactionmost useful commercially? Kc ≈ 0.01, Kc ≈ 1, or Kc ≈ 10. Explain your answerarrow_forwardHow to approach this problem?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
Characteristic Reactions of Benzene and Phenols; Author: Linda Hanson;https://www.youtube.com/watch?v=tjEqEjDd87E;License: Standard YouTube License, CC-BY
An Overview of Aldehydes and Ketones: Crash Course Organic Chemistry #27; Author: Crash Course;https://www.youtube.com/watch?v=-fBPX-4kFlw;License: Standard Youtube License