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Organic Chemistry
11th Edition
ISBN: 9781118133576
Author: T. W. Graham Solomons, Craig Fryhle
Publisher: Wiley, John & Sons, Incorporated
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Chapter SRP, Problem 24P
Interpretation Introduction
Interpretation:
The structure is to be proposed for the compound
Concept introduction:
In
The splitting of the molecules is determined by the
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The treatment of (CH3)2C=CHCH2Br with H2O forms B (molecular formulaC5H10O) as one of the products. Determine the structure of B from its 1H NMR and IR spectra.
The treatment of (CH3)2C=CHCH2Br with H2O forms B (molecular formula C5H10O) as one of the products. Determine the structure of B from its 1H NMR and IR spectra.
(a) The Friedel-Crafts reaction of benzene with 2-chloro-3-methylbutane in the presence of
AlCl3 occurs with a carbocation rearrangement. Give mechanistic explanation and the
product formed.
(b) Predict the product(s) will be formed from the following reactions:
(i) Bromination of p-methylbenzoic acid
(ii) Sulphonation of m-bromoanisole
(iii) Friedel-craft acylation of o-bromonitrobenzene
Chapter SRP Solutions
Organic Chemistry
Ch. SRP - 1. Arrange the compounds of each of the following...Ch. SRP - 2. Arrange the compounds of each of the following...Ch. SRP - Predict the final product from each of the...Ch. SRP - Prob. 4PCh. SRP - Write detailed mechanisms for each of the...Ch. SRP - Prob. 6PCh. SRP - Prob. 7PCh. SRP - Give stereochemical structures for compounds AD:Ch. SRP - Prob. 9PCh. SRP - The remaining steps in the industrial synthesis of...
Ch. SRP - Prob. 11PCh. SRP - Prob. 12PCh. SRP - Prob. 13PCh. SRP - Prob. 14PCh. SRP - 17. Show how you would modify the synthesis given...Ch. SRP - Prob. 16PCh. SRP - Give structures for compounds AD. Compound D gives...Ch. SRP - The tranquilizing drug meprobamate (Equanil or...Ch. SRP - Prob. 19PCh. SRP - 22. Outlined here is the synthesis of a central...Ch. SRP - 23. What are compounds A and B? Compound B has a...Ch. SRP - Prob. 22PCh. SRP - Prob. 26PCh. SRP - 28. Compound Y shows prominent IR absorption...Ch. SRP - Prob. 24PCh. SRP - Consider this reaction involving peracetic acid:...
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- Treatment of benzoic acid (C6H5CO2H) with NaOH followed by 1-iodo-3methylbutane forms H. H has a molecular ion at 192 and IR absorptions at 3064, 3035, 2960−2872, and 1721 cm−1. Propose a structure for H.arrow_forwardTreatment of ketone A with ethynyllithium (HC≡CLi) followed by D3O+ afforded a compound B of molecular formula C12H13DO3, which gave an IR absorption at approximately 1715 cm−1. What is the structure of B and how is it formed?arrow_forwardTreatment of compound E (molecular formula C4H8O2) with excessCH3CH2MgBr yields compound F (molecular formula C6H14O) afterprotonation with H2O. E shows a strong absorption in its IR spectrum at1743 cm−1. F shows a strong IR absorption at 3600−3200 cm−1. The 1HNMR spectral data of E and F are given. What are the structures of E andF?Compound E signals at 1.2 (triplet, 3 H), 2.0 (singlet, 3 H), and 4.1 (quartet, 2 H) ppm Compound F signals at 0.9 (triplet, 6 H), 1.1 (singlet, 3 H), 1.5 (quartet, 4H), and 1.55 (singlet, 1 H) ppmarrow_forward
- Alpha-phellandrene, C₁0H16, is a pleasant-smelling chiral compound that may be obtained from the leaves of eucalyptus trees. It has the molecular formula C₁0H16 and a UV absorption maximum at 263 nm. On hydrogenation with a palladium catalyst, an achiral hydrocarbon with the formula C10H20 is obtained. Ozonolysis of alpha-phellandrene, followed by treatment with zinc and acetic acid, produces the following two compounds: CHIC-CH HOCHSCHICH CH(CH3)2 Propose a structure for alpha-phellandrene.arrow_forwardAlpha-phellandrene, C₁0H₁6, is a pleasant-smelling chiral compound that may be obtained from the leaves of eucalyptus trees. It has the molecular formula C₁0H16 and a UV absorption maximum at 263 nm. On hydrogenation with a palladium catalyst, an achiral hydrocarbon with the formula C₁0H20 is obtained. Ozonolysis of alpha-phellandrene, followed by treatment with zinc and acetic acid, produces the following two compounds: 0 || CH3C-CH 0 || ● Propose a structure for alpha-phellandrene. (+ || HCCH₂CHCH I CH(CH3)2 • You do not have to consider stereochemistry. You do not have to explicitly draw H atoms. • In cases where there is more than one answer, just draw one. n [ ]# ?arrow_forwardCompound C has the molecular formula C;H12. On catalytic hydrogenation, 1 mol of C absorbs 1 mol of hydrogen and yields a compound with the molecular formula C7H14. On ozonolysis and subsequent treatment with zinc and acetic acid, C yields only: The structure of C is:arrow_forward
- -Ocimene is a pleasant-smelling hydrocarbon found in the leaves of certain herbs. It has the molecular formula C10H16 and a UV absorption maximum at 232 nm. On hydrogenation with a palladium catalyst, 2,6-dimethyloctane is obtained. Ozonolysis of -ocimene, followed by treatment with zinc and acetic acid, produces the following four fragments: (a) How many double bonds does -ocimene have? (b) Is -ocimene conjugated or nonconjugated? (c) Propose a structure for -ocimene. (d) Write the reactions, showing starting material and products.arrow_forwardThree compounds, A, B, and C, have the same molecular formula, C5H6. In the presence of a platinum catalyst, all three compounds absorb 3 molar equivalents of hydrogen and yield pentane. Compounds B and C give a precipitate when treated with ammoniacal silver nitrate; compound A give no reaction. Compounds A and B show an absorption maximum near 250 nm. Compound C shows no absorption maximum beyond 200 nm. Propose a structure for A, B, and C.arrow_forwardFuran undergoes electrophilic aromatic substitution more readily than benzene; mild reagents and conditions are sufficient.For example, furan reacts with bromine to give 2-bromofuran.(a) Propose mechanisms for the bromination of furan at the 2-position and at the 3-position. Draw the resonance forms ofeach sigma complex, and compare their stabilities.(b) Explain why furan undergoes bromination (and other electrophilic aromatic substitutions) primarily at the 2-position.O Br O123furan 2-bromofuranarrow_forward
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