(a)
Interpretation:
A sequence of reactions used in the conversion of
Concept introduction:
Carbohydrates are a class of organic compounds. They can be present in the form of open chains or ringsThey are usually an
The six-membered ring form of carbohydrates is termed as pyranose. The five-membered ring form of carbohydrates is termed as furanose.
The pyranoses can be classified as
(b)
Interpretation:
A sequence of reactions used in the conversion of D-glucopyranose to
Concept introduction:
Carbohydrates are a class of organic compounds. They can be present in the form of open chains or rings.
They are usually an aldehyde or ketone with additional hydroxyl groups. They have the general molecular formula,
The 6 membered ring form of carbohydrates is termed as pyranose. This ring contains 5 carbon atoms and 1 an oxygen atom.
The pyranoses can be classified as
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Organic Chemistry
- Thalidomide is a chiral molecule and it was identified that the R-isomerproduced the sedative properties whereas the S-isomer produced the teratogenic effects.Identify the chiral centre in the thalidomide molecule and, using your knowledge of enolisation, illustrate mechanistically, and explain, why there would be no benefit to a patient taking the chirally pure R-isomer of the drug to avoid the sideeffects of the other enantiomer.arrow_forwardAlthough ibuprofen is sold as a racemic mixture, only the S enantiomer acts as an analgesic. In the body, however, some of the R enantiomer is converted to the S isomer by tautomerization to an enol and then protonation to regenerate the carbonyl compound. Write a stepwise mechanism for this isomerization.arrow_forwardFor the following reaction scheme, identify by drawing the reagents b, c, and e, and the intermediate d that are formed in the synthesis of the following carboxylic acid.arrow_forward
- The ketone shown was prepared in a three-step sequence from ethyl trifluoroacetate. The first step in the sequence involved treating ethyl trifluoroacetate with ammonia to give compound A. Compound A was in turn converted to the desired ketone by way of compound B. Fill in the missing reagents in the sequence shown, and give the structures of compounds A and B.arrow_forwardChoose the product that is expected when the β-pyranose form of compound A is treated with excess ethyl iodide in the presence of silver oxide. The following information can be used to determine the identity of compound A: 1. The molecular formula of compound A is C6H12O6.2. Compound A is a reducing sugar.3. When compound A is subjected to a Wohl degradation two times sequentially, D-erythrose is obtained.4. Compound A is epimeric with D-glucose at C3.5. The configuration at C2 is R.arrow_forwardProve that gentiobiose forms osazone and can undergo mutarotation can be hyrolyzed by Emulsin β-glycosidase forms these hydrolysis products following permethylation: 2,3,4,6-tetra-O-methyl-D-glucose and 2,3,4-tri-O-methyl-D-glucosearrow_forward
- when s-2-butanol is allowed to stand in dilute sulfuric acid for several days, it slowly forms a racemic mixture. why this happen and put illustratearrow_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_forwardDraw the product that is expected when the β-pyranose form of compound A is treated with excess ethyl iodide in the presence of silver oxide. The following information can be used to determine the identity of compound A: The molecular formula of compound A is C6H12O6. Compound A is reducing sugar. When compound A is subjected to a Wohl degradation two times sequentially, Derythrose is obtained. Compound A is epimeric with D-glucose at C3. The configuration at C2 is R.EXPLAIN IN DETAIL.arrow_forward
- Draw a line structure clearly showing the stereochemistry of (3S,4S)-4-hydroxy-3,5-dimethylhexanoic acid.arrow_forwardCompound A is an alcohol that undergoes oxidation to produce compound B.Compound B is a ketone that gives positive triiodomethane reaction. Compound B isthen reacted with phenyl magnesium bromide, C6H5MgBr in the presence of aqueousacid to form compound C. Compound C has the molecular formula of C9H12O. Deducethe structure for compound A, B and C. PLEASE PROVIDE CLEAR DRAWINGS AND EXPLANATIONSarrow_forwardTreatment of cholesterol with mCPBA results in formation of a single epoxide A, with the stereochemistry drawn. Why isn’t the isomeric epoxide B formed to any extent?arrow_forward
- Organic ChemistryChemistryISBN:9781305580350Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. FootePublisher:Cengage Learning