Concept explainers
Phenols generally are not changed on treatment with sodium borohydride followed by acidification to destroy the excess, unreacted hydride. For example, the 1,2-, 1,3-, and 1,4-benzenediols and 1,2,3-benzenetriol are unchanged under these conditions. However, 1,3,5-benzenetriol (phloroglucinol) gives a high yield of a product A that has these properties:
MS
IR
(a) What is the structure of A?
(b) Suggest a mechanism by which the above reaction occurred. (1,3,5-Benzenetriol is known to have more tendency to exist in a ketotautomeric form than do simpler phenols.)
Want to see the full answer?
Check out a sample textbook solutionChapter SRP Solutions
ORGANIC CHEMISTRY (LL) W/WILEYPLUS NEXT
Additional Science Textbook Solutions
The Organic Chem Lab Survival Manual: A Student's Guide to Techniques
Fundamentals of Heat and Mass Transfer
Inorganic Chemistry
Living by Chemistry
- Arrange these compounds in order of increasing acidity: 2,4-dichlorophenol, phenol, cyclohexanol.arrow_forwardThe PKa of p-nitrophenol is 7.15. Would you expect this to dissolve in a sodium bicarbonate solution? The PKa of 2,5-dinitrophenol is 5.15. Will it dissolve in bicarbonate solution?arrow_forwardUsing your reaction roadmap as a guide, show how to convert 1-bromopentane and sodium cyanide into N-hexylhexanamide. You must use 1-bromopentane and sodium cyanide as the source of all carbon atoms in the target molecule. Show all reagents and all molecules synthesized along the way.arrow_forward
- Wittig reactions with the following -chloroethers can be used for the synthesis of aldehydes and ketones. (a) Draw the structure of the triphenylphosphonium salt and Wittig reagent formed from each chloroether. (b) Draw the structural formula of the product formed by treating each Wittig reagent with cyclopentanone. Note that the functional group is an enol ether or, alternatively, a vinyl ether. (c) Draw the structural formula of the product formed on acid-catalyzed hydrolysis of each enol ether from part (b).arrow_forwardReaction of p-nitroaniline with sodium nitrite and hydrochloric acid at 0°C, followed by treatment with N,N-diethylaniline.arrow_forwardShow how to convert cyclopentanone to these compounds. In addition to cyclopentanone, use any other organic or inorganic reagents as necessary.arrow_forward
- The following questions concern ethyl (2-oxocyclohexane)carboxylate.(a) Write a chemical equation showing how you could prepare ethyl (2-oxocyclohexane)-carboxylate by a Dieckmann cyclization.(b) Write a chemical equation showing how you could prepare ethyl (2-oxocyclohexane)-carboxylate by acylation of a ketone.(c) Write structural formulas for the two most stable enol forms of ethyl (2-oxocyclohexane)carboxylate.(d) Write the three most stable resonance contributors to the most stable enolate derived from ethyl (2-oxocyclohexane)carboxylate.(e) Show how you could use ethyl (2-oxocyclohexane)carboxylate to prepare 2-methylcyclohexanone.(f) Give the structure of the product formed on treatment of ethyl (2-oxocyclohexane)-carboxylate with acrolein (H2C=CHCH=O) in ethanol in the presence of sodium ethoxidearrow_forwardWrite an equation for the reaction (if any) of benzaldehyde with each of the following reagents: - a) Tollen's reagent b) hydroxylamine c) ethyl magnesium bromide, then H3O+ d) phenylhydrazine e) HCN f) excess methanol, H+ g) LiAlH4 h) ethylene glycol, H+arrow_forwardSketch and explain the IR, UV, mass, and NMR (1H and 13C) spectroscopy data of benzaldehyde.arrow_forward
- Sketch and explain the IR, UV, mass, and NMR (1H and 13C) spectroscopy data of Benzonitrilearrow_forwardPyrrole reacts with excess para-(N,N-dimethylamino)benzaldehyde to form a highly colored compound. Draw the structure of the colored compound.arrow_forwardTreatment of cis-4-bromocyclohexanol with HO– affords compound A and cyclohex-3-en-1-ol. Treatment of trans-4- bromocyclohexanol under the same conditions forms compound B and cyclohex-3-en-1-ol. A and B contain different functional groups and are not isomers of each other. Propose structures for A and B and offer an explanation for their formation.arrow_forward
- Macroscale and Microscale Organic ExperimentsChemistryISBN:9781305577190Author:Kenneth L. Williamson, Katherine M. MastersPublisher:Brooks ColeOrganic ChemistryChemistryISBN:9781305580350Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. FootePublisher:Cengage Learning