Concept explainers
Interpretation:
The product obtained from the Wittig reaction has to be identified.
Concept introduction:
Alkyl bromide reacts with triphenylphosphine to form triphenylphosphonium salt. The salt is further treated with base to from phosphonium ylide. Phosphonium ylide reacts with
The
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Chapter 16 Solutions
Organic Chemistry, Books a la Carte Edition (8th Edition)
- 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.arrow_forwardKetones undergo a reduction when treated with sodium borohydride, NaBH4. What is the structure of the compound produced by reaction of 2-butanone with NaBH4 if it has an IR absorption at 3400 cm-1 and M+=74 in the mass spectrum?arrow_forwardEnamines normally react with methyl iodide to give two products: one arising from alkylation at nitrogen and the second arising from alkylation at carbon. For example, Heating the mixture of C-alkylation and N-alkylation products gives only the product from C-alkylation. Propose a mechanism for this isomerization.arrow_forward
- Compound I (C11H14O2) is insoluble in water, aqueous acid, and aqueous NaHCO3, but dissolves readily in 10% Na2CO3 and 10% NaOH. When these alkaline solutions are acidified with 10% HCl, compound I is recovered unchanged. Given this information and its 1H-NMR spectrum, deduce the structure of compound I.arrow_forwardCompound H (C8H6O3) gives a precipitate when treated with hydroxylamine in aqueous ethanol and a silver mirror when treated with Tollens solution. Following is its 1H-NMR spectrum. Deduce the structure of compound H.arrow_forwardAs a method for the synthesis of cinnamaldehyde (3-phenyl-2-propenal), a chemist treated 3-phenyl-2-propen-1-ol with K2Cr2O7 in sulfuric acid. The product obtained from the reaction gave a signal at δ5 in its 13C NMR spectrum. Alternatively, when the chemist treated 3-phenyl-2-propen-1-ol with PCC in CH2Cl2, the 13C NMR spectrum of the product displayed a signal at δ193.8. (All other signals in the spectra of both compounds appeared at similar chemical shifts.) (a) Which reaction produced cinnamaldehyde? (b) What was the other product?arrow_forward
- Identify products A and B from the given 1H NMR data. Treatment of acetone [(CH3)2C=O] with dilute aqueous base forms B. Compound B exhibits four singlets in its 1H NMR spectrum at 1.3 (6 H), 2.2 (3 H), 2.5 (2 H), and 3.8 (1H) ppm. What is the structure of B?arrow_forwardIdentify products A and B from the given 1H NMR data. Treatment of CH2=CHCOCH3 with one equivalent of HCl forms compound A. A exhibits the following absorptions in its 1H NMR spectrum: 2.2 (singlet, 3H), 3.05 (triplet, 2 H), and 3.6 (triplet, 2 H) ppm. What is the structure of A?arrow_forwardAfter 2-bromo-3,3-dimethylbutane was reacted with H2SO4, a ¹H NMR spectrum was obtained of the product. This spectrum showed a singlet at 1.79 ppm. Propose a structure for the product of this reaction. OH H2SO4 Qarrow_forward
- Acid-catalyzed dehydrarion of 3-hydroxy-3-phenylcyctohexanone leads to an unsaturated ketone. What possible structures are there for the product? At what position in the IR spectrum would you expect each to absorb? If the actual product has an absorption at 1670 cm', what is its structure ?arrow_forwardA compound gives the following IR spectrum. Upon reaction with sodium borohydride followed by acidification, it forms the product with the 1H NMRspectrum shown below. Identify the starting material and the product.arrow_forward
- Organic ChemistryChemistryISBN:9781305580350Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. FootePublisher:Cengage Learning