The reaction of 1-methylcyclopentene withmercuric trifluoroacetate inethanol followed by reductionwith sodium borohydride gives1-ethoxy-1-methylcyclopentane.The -OH peak in the IR showsup at 1700 cm-1 as a sharppeak.(S)-2-bromohexane is theproduct of the reaction of(S)-2-hexanol with PBr3.The 1H NMR spectrum of 1-pentanol will show a peak forthe H atom of the -OH groupat 10 ppm delta.A tosylate is a great protectinggroup for an alcohol.The Williamson ether synthesisis an SN2 reaction of analkoxide ion with a primaryalkyl halide.Thionyl chloride convertsketones into alkyl halides.In an oxidation reaction, theoxygen content of our organicmolecule decreases.✓ [Choose ]FalseTrue[Choose ][Choose ][Choose ][Choose ][Choose ][Choose ][Choose ]

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The reaction of 1- methylcyclopentene with mercuric trifluoroacetate in ethanol followed by reduction with sodium borohydride gives 1-ethoxy-1- methylcyclopentane. The -OH peak in the IR shows up at 1700 cm-1 as a sharp peak. (S)-2-bromohexane is the product of the reaction of (S)-2-hexanol with PBr3. [Choose ] False True [Choose ] [Choose ] >

The reaction of 1- methylcyclopentene with mercuric trifluoroacetate in ethanol followed by reduction with sodium borohydride gives 1-ethoxy-1- methylcyclopentane. The -OH peak in the IR shows up at 1700 cm-1 as a sharp peak. (S)-2-bromohexane is the product of the reaction of (S)-2-hexanol with PBr3. [Choose ] False True [Choose ] [Choose ] >

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

Chapter11: Ethers, Epoxides, And Sulfides

Section: Chapter Questions

Problem 11.24P: The following equation shows the reaction of trans-2,3-diphenyloxirane with hydrogen chloride in...

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Reaction of p-cresol with two equivalents of 2-methylprop-1-ene affords BHT, a preservative with molecular formula C15H24O. BHT gives the following 1H NMR spectral data: 1.4 (singlet, 18 H), 2.27 (singlet, 3 H), 5.0 (singlet, 1 H), and 7.0 (singlet, 2 H) ppm. What is the structure of BHT? Draw a stepwise mechanism illustrating how it is formed.
The base-promoted rearrangement of an -haloketone to a carboxylic acid, known as the Favorskii rearrangement, is illustrated by the conversion of 2-chlorocyclohexanone to cyclopentanecarboxylic acid. It is proposed that NaOH first converts the a-haloketone to the substituted cyclopropanone shown in brackets and then to the sodium salt of cyclopentanecarboxylic acid. (a) Propose a mechanism for base-promoted conversion of 2-chlorocyclohexanone to the proposed intermediate. (b) Propose a mechanism for base-promoted conversion of the proposed intermediate to sodium cyclopentanecarboxylate.
The following equation shows the reaction of trans-2,3-diphenyloxirane with hydrogen chloride in benzene to form 2-chloro-1,2-diphenylethanol. (a) How many stereoisomers are possible for 2-chloro-1,2-diphenylethanol? (b) Given that opening of the epoxide ring in this reaction is stereoselective, predict which of the possible stereoisomers of 2-chloro-1,2-diphenylethanol is/are formed in the reaction.
-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.
Treatment of isobutene [(CH3)2C=CH2] with (CH3)3CLi forms a carbanion that reacts with CH2=O to form H after water is added to the reaction mixture. H has a molecular ion in its mass spectrum at m/z = 86, and shows fragments at 71 and 68. H exhibits absorptions in its IR spectrum at 3600−3200 and 1651 cm−1, and has the 1H NMR spectrum given below. What is the structure of H?
Reaction of p-cresol with two equivalents of 2-methylprop-1-ene affordsBHT, a preservative with molecular formula C15H24O. BHT gives thefollowing 1H NMR spectral data: 1.4 (singlet, 18 H), 2.27 (singlet, 3 H), 5.0(singlet, 1 H), and 7.0 (singlet, 2 H) ppm. What is the structure of BHT?Draw a stepwise mechanism illustrating how it is formed.
The reaction of (R)-1-bromobutane with Lil in DMF yields: (S)-1-lodobutane (S)-2-lodobutane (R)-1-lodobutane 2-butene Choose the best reagent(s) for carrying out the conversion of the reaction below CH,CH-снсH,cоон сн,сон + носсн,соон NABH, ethanol B) KMNO, Hy,0 (1) BH, (2) H,0" 0, Zn/H,0 Arrange the following compounds in decreasing order of reactivity towards Nal in acetone: L. Methyt bromide I. Isopropyl bromide I. Ethyl bromide IV. t-butyl bromide A V, I, I, I B), II, II, IV IV, II, II, I LIL, II, IV A hydrocarbon (Y) partially hydrogenates with the Lindlar's catalyst to form an alkene. When (Y) undergoes axidative cleavage with ozone, it yields a singe carboxylic acid product. The hydrocarbon (M is: 2-hexen-1-ol 2-hexyne 2-butyne cyclohexane
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Rimantadine was among the first antiviral drugs to be licensed in the United States to use against the influenza A virus and to treat established illnesses. It is synthesized from adamantane by the following sequence: CH₂=CHBr AlBr3 (2) Adamantane =D₂.-6. (3) -Br Br (4) Ø Br₂ (1) a Step 2 proceeds via the following mechanism: 1-bromoadamantane (5) Br SnF ChemDoodle Rimantadine 1. AlBr, acts as a Lewis acid to yield carbocation 1; 2. Bromoethene acts as a nucleophile to give carbocation 2; 3. Carbocation 2 reacts with nucleophile 3 to give the product of reaction 2. Work out this mechanism on a separate sheet of paper and then draw the structure of nucleophile 3. NH₂ ==starting points == ✔
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