Alkyne anions react with the carbonyl groups of aldehydes and ketones to form alkynylalcohols, as illustrated by the following sequence.HCICH,C=C Na* + H-C-H [CH,C=C-CH,O Na*]H,O→ CH,C=C-CH,OHPropose a mechanism for the formation of the bracketed compound, using curved arrowsto show the flow of electron pairs in the course of the reaction.

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Answered: Alkyne anions react with the carbonyl…

Organic Chemistry

8th Edition

ISBN:9781305580350

Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote

Publisher:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote

Chapter7: Alkynes

Section: Chapter Questions

Problem 7.26P

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Reaction of 2-methylpropene with CH3OH in the presence of H2SO4 catalyst yieldsmethyl tert-butyl ether, CH3OC(CH3)3, by a mechanism analogous to that of acid- catalyzed alkene hydration. Write the mechanism, using curved arrows for each step.
Propose the structure of the following: a. An alkane, C6H14 b. A crylic saturated hydrocarbon, C6H12 c. A diene (dialkene), C5H8 d. A keto alkene, C5H8O
Alkenes can be hydrated to form alcohols by (1) hydroboration followed by oxidation with alkaline hydrogen peroxide and (2) acid-catalyzed hydration. Compare the product formed from each alkene by sequence (1) with those formed from (2). Q.)1-Methylcyclohexene
5. Compound A, C 10H 18O, undergoes reaction with dilute H 2SO 4 at 50 °C to yield a mixture of two alkenes, C 10H 16. The major alkene B, gives only cyclopentanone after ozone treatment followed by reduction with zinc in acetic acid. Which of the following reactions are correct.
Nitromethane is reacted with ethyl prop-2-enoate with EtO-Na+, EtOH 3 equivalents to give the product X(C16). X then reacts with H2/Raney Ni to give the product Y(C14), which in turn reacts with Na to give Z (C12). Indicate which products X, Y and Z are.
Compound AA has a molecular formula of C3H6O and gives a positiveresult using Tollen’s reagent. The reaction of compound AA with hotacidified potassium permanganate, KMnO4 gives compound BB. Thecatalytic hydrogenation of compound AA with nickel, Ni producedcompound CC. The reaction of compound BB with ethanamine,CH3CH2NH2 produces compound DD I) Draw the structural formula of compounds AA, BB, CC and DD. 2)Name the type of chemical reaction for the formation of compound CC.
1. Deduce the structure of each compound from the information given. All unknowns in this problem have molecular formula C8H12. (a) Upon catalytic hydrogenation, unknown W gives cyclooctane. Ozonolysis of W, followed by reduction with dimethylsulfide, gives octanedioic acid, HOOC—(CH2)6—COOH. Draw the structure of W. (b) Upon catalytic hydrogenation, unknown X gives cyclooctane. Ozonolysis of X, followed by reduction with dimethyl sulfide, gives two equivalents of butanedial, O=CH—CH2CH2—CH=O. Draw the structure of X.
A chemist allows some pure (2S,3R)-3-bromo-2,3-diphenylpentane to react with a solution of sodium ethoxide(NaOCH2 CH3) in ethanol. The products are two alkenes: A (cis-trans mixture) and B, a single pure isomer. Under the same conditions, the reaction of (2S,3S)-3-bromo-2,3-diphenylpentane gives two alkenes, A (cis-trans mixture) and C. Upon catalytic hydrogenation, all three of these alkenes (A, B, and C) give 2,3-diphenylpentane. Determine the structures of A, B, and C; give equations for their formation; and explain the stereospecificity of these reactions.
4. Compound A has the formula C 8H 8. It reacts rapidly with KMnO 4 to give CO 2 and a carboxylic acid, B (C 7H 6O 2), but reacts with only 1 molar equivalent of H 2 on catalytic hydrogenation over a palladium catalyst. On hydrogenation under conditions that reduce aromatic rings, 4, equivalents of H 2 are taken up and hydrocarbon C (C 8H 16) is produced. What are the structures of A, B, and C.
An unknown hydrocarbon Q has a formula C6H12. Q reacts with osmium tetroxide to give a diol R when oxidized with KMnQ4 in an acidic medium Q gives two products. One product is propanoic acid and the other is ketone S. Provide reaction equations to identify the possible structures of Q, R and S.
One frequently used method for preparing methyl esters is by reaction of carboxylic acids with diazomethane, CH2N2. The reaction occurs in two steps: (l) protonation of diazomethane by the carboxylic acid to yield methyldiazonium ion, CH3N2+, plus a carboxylate ion; and (2) reaction of the carboxylate ion with CH3N2+. (a) Draw two resonance structures of diazomethane, and account for step 1. (b) What kind of reaction occurs in step 2?
Reaction of iodoethane with CN- yields a small amount of isonitrile, CH3CH2Nâ‰¡C, along with the nitrile CH3CH2Nâ‰¡N, as the major product. Write electron-dot structures for both products, assign formal charges as necessary, and propose mechanisms to account for their formation.

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