Concept explainers
Interpretation:
The constitution of the given material having the molecular formula
Concept Introduction:
>Ozonolysis of
If formaldehyde is produced after ozonolysis, it can be deduced that the alkene has a terminal double bond.
>If an aldehyde is produced after ozonolysis, at least one of the double bonded carbon atoms in the alkene has a hydrogen attached to it.
>If a ketone is produced after ozonolysis, at least one of the double bonded carbon atoms in the alkene must be disubstituted.
>Catalytic hydrogenation of alkenes leads to the production of
Want to see the full answer?
Check out a sample textbook solutionChapter 8 Solutions
ORGANIC CHEMISTRY TEXT PACKAGED - 2 YE
- Following is a retrosynthesis for the coronary vasodilator ganglefene. (a) Propose a synthesis for ganglefene from 4-hydroxybenzoic acid and 3-methyl-3-buten-2-one. (b) Is ganglefene chiral? If so, which of the possible stereoisomers are formed in this synthesis?arrow_forwardEleostearic acid, C18H30O2, is a rare fatty acid found in the tung oil used for finishing furniture. On ozonolysis followed by treatment with zinc, eleostearic acid furnishes one part pentanal, two parts glyoxal (OHC-CHO), and one part 9-oxononanoic acid [OHC(CH2)7CO2H]. What is the structure of eleostearic acid?arrow_forwardIsoerythrogenic acid, C18H26O2, is a acetylic fatty acid that turns vivid vle on exposure to UV light. On Catalytic hydrogenation over a palladium catalyst, five molar equivalents of hydrogen are absorbed, and stearic acidarrow_forward
- Compound X is optically inactive and has the formula C 16H 16Br 2. On treatment with strong base, X gives hydrocarbon Y, C 16H 14. Compound Y absorbs 2 equivalents of hydrogen when reduced over a palladium catalyst and reacts with ozone to give two fragments. One fragment Z, is an aldehyde with formula C 7H 6O. The other fragment is glyoxal, (CHO)2. Which of the following answers is correct? Select all that are correct.arrow_forwardDraw a line structure clearly showing the stereochemistry of (3S,4S)-4-hydroxy-3,5-dimethylhexanoic acid.arrow_forwardSeveral 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.arrow_forward
- The tartaness of some wines is high concentration of l malate.write a consequence of reactions showing how yeast cells synthesize l malate from glucose under anaerobic conditions in the presence of co2arrow_forwardBased on the following H NMR and IR spectrums, what is the structure of C9H8O4?arrow_forward(i) What is meant by chirality of a compound? Give an example.(ii) Which one of the following compounds is more easily hydrolyzed by KOH and why?CH3CHClCH2CH3 or CH3CH2CH2Clarrow_forward
- The sex attractant of the female arctiid moth contains, among other components, a compound of molecular formula C21H40 that yields on ozonolysis. What is the constitution of this material?arrow_forwardBetamethasone is a synthetic anti-inflammatory steroid used as a topical cream for itching. Betamethasone is derived from cortisol, with the following structural additions: a C=C between C1 and C2, a fluorine at C9, and a methyl group at C16. The configuration at C9 is R, and the configuration at C16 is S. Draw the structure of betamethasone.arrow_forwardWhen the gum of the shrub Sterculia setigera is subjected to acidic hydrolysis, one of the water-soluble components of thehydrolysate is found to be tagatose. The following information is known about tagatose:(1) Molecular formula C6H12O6(2) Undergoes mutarotation.(3) Does not react with bromine water.(4) Reduces Tollens reagent to give d-galactonic acid and d-talonic acid.(5) Methylation of tagatose (using excess CH3 I and Ag2O) followed by acidic hydrolysis gives1,3,4,5-tetra-O-methyltagatose.(a) Draw a Fischer projection structure for the open-chain form of tagatose.(b) Draw the most stable conformation of the most stable cyclic hemiacetal form of tagatosearrow_forward
- Organic ChemistryChemistryISBN:9781305580350Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. FootePublisher:Cengage LearningIntroduction to General, Organic and BiochemistryChemistryISBN:9781285869759Author:Frederick A. Bettelheim, William H. Brown, Mary K. Campbell, Shawn O. Farrell, Omar TorresPublisher:Cengage Learning