When acetonitrile is treated with concentrated sulfuric acid and tert-butanol, followed by water, a product is formedwhose 'H NMR spectrum exhibits the following three signals: singlet, 1.3 ppm, 9 H; singlet, 2.0 ppm, 3 H; andbroad singlet, 8.2 ppm, 1 H. Its IR spectrum exhibits one broad absorption of medium intensity between 3300 and3500 cm-1, and a narrow, intense absorption near 1650 cm¯1. A key intermediate is shown. Draw the structure ofthe product, and draw the complete, detailed mechanism for the reaction.CH3CH3H2SO4 (conc)H2O?+ H3CH3CH3C-C=Ñ-c`CH3CH3HO

Answered: When acetonitrile is treated with…

Organic Chemistry

9th Edition

ISBN:9781305080485

Author:John E. McMurry

Publisher:John E. McMurry

Chapter27: Biomolecules: Lipids

Section27.SE: Something Extra

Problem 47AP: Cembrene, C20H32, is a diterpenoid hydrocarbon isolated from pine resin. Cembrene has a UV...

See similar textbooks

Similar questions

Ibufenac, a para-disubstituted arene with the structure HO2CCH26H4CH2CH(CH3)2, is a much more potent analgesic than aspirin, but it was never sold commercially because it caused liver toxicity in some clinical trials. Devise a synthesis of ibufenac from benzene and organic halides having fewer than five carbons.
The treatment of isoprene [CH2=C(CH3)CH=CH2] with one equivalent ofmCPBA forms A as the major product. A gives a molecular ion at 84 in itsmass spectrum, and peaks at 2850–3150 cm−1 in its IR spectrum. The 1HNMR spectrum of A is given below. What is the structure of A?
Cembrene, C20H32, is a diterpenoid hydrocarbon isolated from pine resin. Cembrene has a UV absorption at 245 nm, but dihydrocembrene (C20H34), the product of hydrogenation with 1 equivalent of H2, has no UV absorption. On exhaustive hydrogenation, 4 equivalents of H2 react, and octahydrocembrene, C20H40, is produced. On ozonolysis of cembrene, followed by treatment of the ozonide with zinc, four carbonylcontaining products are obtained: Propose a structure for cembrene that is consistent with its formation from geranylgeranyl diphosphate.
β-ocimene is a pleasant smelling hydrocarbon found in the leaves of a certain herbs. It has a molecular formula C10H16 and a UV absorption λmax 232nm. On hydrogenation with a palladium catalyst, 2,6-dimethyloctane is obtained. Ozonolysis β-ocimene followed by the treatment with zinc and acetic acid produces the following fragments:
Several sulfonylureas, a class of compounds containing RSO2NHCONHR, are useful drugs as orally active replacements for injected insulin in patients with adult-onset diabetes. These drugs decrease blood glucose concentrations by stimulating b cells of the pancreas to release insulin and by increasing the sensitivity of insulin receptors in peripheral tissues to insulin stimulation. Tolbutamide is synthesized by the reaction of the sodium salt of p-toluenesulfonamide and ethyl N-butylcarbamate . Propose a mechanism for this step.
Propose a structural formula for compound A, C5H13N, given its IR and calculated 1H-NMR spectra.
Oxidation of cholesterol converts the alcohol to a ketone. Under acidic or basic oxidationconditions, the C“C double bond migrates to the more stable, conjugated position. BeforeIR and NMR spectroscopy, chemists watched the UV spectrum of the reaction mixture tofollow the oxidation. Describe how the UV spectrum of the conjugated product, cholest-4-en-3-one, differs from that of cholesterol
Reaction of (CH3)3CCHO with (C6H5)3P=C(CH3)OCH3, followed bytreatment with aqueous acid, affords R (C7H14O). R has a strong absorption in its IR spectrum at 1717 cm−1 and three singlets in its 1H NMR spectrum at 1.02 (9 H), 2.13 (3 H), and 2.33 (2 H) ppm. What is thestructure of R?
A compound with molecular formula C5H10O2 gives the following IR spectrum. When it undergoes acid-catalyzed hydrolysis, the compound with the 1H NMR spectrum shown below is formed. Identify the compounds.
An ether extraction of nutmeg gives large quantities of trimyristin, a waxy crystalline solid of melting point 57 °C. The IRspectrum of trimyristin shows a very strong absorption at 1733 cm-1. Basic hydrolysis of trimyristin gives 1 equivalent ofglycerol and 3 equivalents of myristic acid (tetradecanoic acid).(a) Draw the structure of trimyristin.(b) Predict the products formed when trimyristin is treated with lithium aluminum hydride, followed by aqueous hydrolysis of the aluminum salts
Heating compound X with aqueous formaldehyde forms Y (C17H23NO),which has been converted to a mixture of lupinine and epilupinine,alkaloids isolated from lupin, a perennial ornamental plant commonlyseen on the roadside in parts of Alaska . Identify Y and explain how it is formed.

Recommended textbooks for you

Organic Chemistry

Chemistry

ISBN:

9781305080485

Author:

John E. McMurry

Publisher:

Cengage Learning

Organic Chemistry

Chemistry

ISBN:

9781305580350

Author:

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

Publisher:

Cengage Learning

Organic Chemistry

Chemistry

ISBN:

9781305080485

Author:

John E. McMurry

Publisher:

Cengage Learning

Organic Chemistry

Chemistry

ISBN:

9781305580350

Author:

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

Publisher:

Cengage Learning

SEE MORE TEXTBOOKS