Organic Chemistry - Standalone book
10th Edition
ISBN: 9780073511214
Author: Francis A Carey Dr., Robert M. Giuliano
Publisher: McGraw-Hill Education
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Chapter 15, Problem 33P
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In a basic aqueous solution, esters react with hydroxide ion to form the salt of the carboxylic acid and the alcohol from which the
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Chapter 15 Solutions
Organic Chemistry - Standalone book
Ch. 15.1 - Each of the following organometallic reagents will...Ch. 15.3 - Write equations showing how you could prepare...Ch. 15.4 - Lithium diisopropylamide is often used as a strong...Ch. 15.5 - Write the structure of the organic product of each...Ch. 15.7 - Prob. 5PCh. 15.8 - Prob. 6PCh. 15.9 - Prob. 7PCh. 15.9 - Like nickel, iron reacts with carbon monoxide to...Ch. 15.9 - Prob. 9PCh. 15.9 - What is the oxidation state of manganese in the...
Ch. 15.9 - Prob. 11PCh. 15.10 - Prob. 12PCh. 15.10 - Prob. 13PCh. 15.11 - Give the structure including stereochemistry of...Ch. 15.11 - Prob. 15PCh. 15.12 - Homogeneous catalytic hydrogenation of the...Ch. 15.12 - Prob. 17PCh. 15.13 - What alkenes are formed from 2-pentene by olefin...Ch. 15.13 - The product of the following reaction was isolated...Ch. 15 - Suggest appropriate methods for preparing each of...Ch. 15 - Prob. 21PCh. 15 - Predict the principal organic product of each of...Ch. 15 - Prob. 23PCh. 15 - Predict the principal organic product of each of...Ch. 15 - Prob. 25PCh. 15 - A different stereoisomer of...Ch. 15 - Prob. 27PCh. 15 - Using phenyllithium and any necessary organic or...Ch. 15 - Prob. 29PCh. 15 - A number of drugs are prepared by reactions in...Ch. 15 - The following conversion was carried out in two...Ch. 15 - Outline syntheses of (a)...Ch. 15 - (S)-(+)-Ibuprofen can be prepared by...Ch. 15 - Like other hydroborations, the reaction of alkynes...Ch. 15 - The sex attractant of the female silkworm has been...Ch. 15 - Prob. 36PCh. 15 - (a) Exaltolide, a musk substance, has been...Ch. 15 - Prob. 38PCh. 15 - Prob. 39PCh. 15 - Cyclobutadiene and...Ch. 15 - Cyclobutadiene and (Cyclobutadiene)tricarbonyliron...Ch. 15 - Cyclobutadiene and...Ch. 15 - Cyclobutadiene and...Ch. 15 - Cyclobutadiene and...
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- Hydrocarbon A has the molecular formula C14H10C12. It absorbs eight molar equivalents of any hydrogen isotope using a Nickel catalyst. When subjected to ozonolysis, Compound A yields oxalic acid and the chiral chloropentane dioic acid. Write the reactions and propose a structure for A.arrow_forwardBiphenyl has the following structure.(a) Is biphenyl a (fused) polynuclear aromatic hydrocarbon?(b) How many pi electrons are there in the two aromatic rings of biphenyl? How does this number compare with that for naphthalene?(c) The heat of hydrogenation for biphenyl is about 418 kJ>mol (100 kcal>mol). Calculate theresonance energy of biphenyl.(d) Compare the resonance energy of biphenyl with that of naphthalene and with that of two benzene rings. Explain thedifference in the resonance energies of naphthalene and biphenyl.arrow_forwardA chemist synthesized compound X as a racemic mixture. When the ketone group in X was enzymatically reduced to the corresponding alcohol, a 100% yield was obtained of the product shown below. Choose the statement that best describes this result. ОН enzyme C;H1 `OCH,CH; pH 4.0 C3H1 `OCH,CH3 ОН ÕH X (racemic) (100% yield) One enantiomer of compound X reacts quickly with the enzyme. The other enantiomer of compound X is unreactive, but rapidly equilibrates with the reactive enantiomer under the reaction conditions. Since compound X was racemic, it makes sense that only a single product was obtained. O The product is a meso compound, so either enantiomer of compound X gives the same product. One enantiomer of compound X reacts quickly with the enzyme, while the other enantiomer of compound X remains unchanged.arrow_forward
- (a) Draw the three isomers of benzenedicarboxylic acid.(b) The isomers have melting points of 210 °C, 343 °C, and 427 °C. Nitration of the isomers at all possible positions was once used to determine their structures. The isomer that melts at 210 °C gives two mononitro isomers. The isomer that melts at 343 °C gives three mononitro isomers. The isomer that melts at 427 °C gives only one mononitro isomer. Show which isomer has which melting point.arrow_forward(a) Chromic acid oxidation of 4-tert-butyl-1,2-dimethylbenzene yielded a single compound having the molecular formula C12H14O4. What was this compound?(b) What product is expected from chromic acid oxidation of 2,3-dihydroindene?arrow_forward(a) Draw the structure of the following :(i) p-Methylbenzaldehyde (ii) 4-Methylpent-3-en-2-one(b) Give chemical tests to distinguish between the following pairs of compounds :(i) Benzoic acid and Ethyl benzoate, (ii) Benzaldehyde and Acetophenone.(iii) Phenol and Benzoic acid.arrow_forward
- An aromatic compound K, whose molecular formula is C8H11N, is examined in the laboratory to elucidate its structure. The following observations were made: A) Compound K is soluble in dilute hydrochloric acid but insoluble in sodium hydroxide solution. B) Treatment of compound K with excess potassium hydroxide and benzenesulfonyl chloride, C(6)H(5)SO(2)Cl, results in the formation of a heterogeneous mixture. The NMR spectrum of compound K is shown below. C) Compound K when treated with acetic anhydride[CH3-C(O)-O-C(O)-CH3], gives compound L, whose molecular formula is C(10)H(13)ON. Compound L is insoluble in dilute acid or dilute base at room temperature, heating compound L in dilute acid or base, however, regenerates compound K. D) When compound L is heated with a mixture of concentrated nitric acid and sulfuric acid, a single product, compound M, with the molecular formula C(10)H(12)O(3)N(2) is formed in excellent yields. On the basis of these observations draw the structures of…arrow_forwardWrite chemical equations of the reactions of ethanoic acid with(a) Sodium(b) Sodium carbonate(c) Ethanol in the presence of conc. H2SO4arrow_forward(b) 3-methyl-2-butanol reacts with concentrated sulphuric acid to form 2-methyl-2- butene. Write the mechanism for the reaction.arrow_forward
- Which of the following statements about 3-iodo-2-methylprop-1-ene is/are true? (i) It has an E isomer and a Z isomer. (ii) It can be converted to an alkyl lithium compound in one step by reacting with lithium metal. (iii) It would react with the following reagent to give 2-methylhept-1-ene as the product: CuLiarrow_forwardwe saw that Agent Orange contains (2,4,5-trichlorophenoxy) acetic acid, called 2,4,5-T. This compound is synthesized by the partial reaction of 1,2,4,5-tetrachlorobenzene with sodium hydroxide, followed by reaction with sodium chloroacetate, ClCH2CO2Na.(a) Draw the structures of these compounds, and write equations for these reactions.(b) One of the impurities in the Agent Orange used in Vietnam was 2,3,7,8-tetrachlorodibenzodioxin (2,3,7,8-TCDD), often incorrectly called “dioxin.” Propose a mechanism to show how 2,3,7,8-TCDD is formed in the synthesis of 2,4,5-T.(c) Show how the TCDD contamination might be eliminated, both after the first step and on completion of the synthesis.arrow_forwardDraw the structure of the predominant form of CF3CH2OH (pK a = 12.4) at pH = 6.arrow_forward
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