Interpretation:
Based on the given information, the structures of compounds A-F are to be proposed.
Concept introduction:
A carbohydrate is a
The Ruff degradation reaction is used for decreasing the number of carbon atoms of the respective aldoses, thereby shortening the carbon chain of the compound. It works in two steps:
Using bromine water to oxidize an aldose to the respective aldonic acid.
Using
The Kiliani-Fischer reaction is used for producing epimers of higher aldoses from a lower aldose.
Alditols are sugar alcohols formed by the addition of hydrogen to the monosaccharide. Reduction of monosaccharides (carbohydrates containing single units of sugar molecules) results in the formation of alditols.
The molecules that are non-superimposable or not identical with their mirror images are known as chiral molecules.
A pair of two mirror images that are non-identical are known as enantiomers, which are optically active.
The stereoisomers that are non-superimposable on each other and not mirror images of each other are known as diastereomers.
The achiral compounds in which plane of symmetry is present internally and consists of chiral centres are known as meso compounds, but they are optically inactive.
Compounds that have a plane of symmetry tend to exist in meso forms. A meso form arises when the two stereoisomers produce superimposable images, and hence, compounds having meso forms are optically inactive.
Want to see the full answer?
Check out a sample textbook solutionChapter 22 Solutions
EBK ORGANIC CHEMISTRY
- (S)-Glutamic acid is one of the 20 amino acid building blocks of polypeptides and proteins (Chapter 27). Propose a mechanism for the following conversion.arrow_forwardFollowing 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_forwardNaturally occurring compounds called cyanogenic glycosides, such as lotaustralin, release hydrogen cyanide, HCN, when treated with aqueous acid. The reaction occurs by hydrolysis of the acetal linkage to form a cyanohydrin, which then expels HCN and gives a carbonyl compound. (a) Show the mechanism of the acetal hydrolysis and the structure of the cyanohydrin that results. (b) Propose a mechanism for the loss of HCN, and show the structure of the carbonyl compound that forms.arrow_forward
- Treatment of α,β-unsaturated carbonyl compound X with base forms the diastereomer Y. Write a stepwise mechanism for this reaction. Explain why one stereogenic center changes configuration but the other does not.arrow_forwardEsters with only one a hydrogen generally give poor yields in the Claisen condensation.Propose a mechanism for the Claisen condensation of ethyl isobutyrate, and explain whya poor yield is obtained.arrow_forwardSynthesize the compund (Nimodipine) via Hantzsch dihydropyridine synthesisarrow_forward
- A hexose is obtained when the residue of a shrub Sterculia setigeria undergoes acid-catalyzed hydrolysis. Identify the hexose from the following experimental information: it undergoes mutarotation; it does not react with Br2; and D-galactonic acid and D-talonic acid are formed when it reacts with Tollens’ reagent.arrow_forwardtrehalose is a disacharide that can be obtained from fungi sea uchins and insects. acid hydrolysis of trehalose yields only D-glucose. trehalose is hydrolysed by a-glucosidase but not b-glucosidase.methylation of trhalose followed by hydrolysis yield two molar equivalents of 2-3-4-6 -tetra-O-methyl-D-glucopyranose. deduce the structure of the trehalose using the experimental dataarrow_forwardMyo-inositol, the most prominent naturally occurring form of inositols, is a carbocyclic polyol that plays an important role as the structural basis for a number of secondary messengers in eukaryotic cells. It is generated in vivo from the aldol cyclization of glucose-6-phosphate to myo-inositol-1-phosphatearrow_forward
- Provide a selective synthesisarrow_forward2305032118517 CHO H-C-OH H-C-OH H₂C₂OH CHO Ho-C-tt A D-aldotetrose yields a mixture of the two compounds shown below when subjected to Kiliani - Fischer Chain extension synthesis. What is the Structure of the aldotetrose? 3 CH₂OH Compound I H-C-OH CHO HO-C-H Ho C-H сно HO-C-H WOO Н-С-он H-C-OH CH ₂ OH Compound II CHO H² C-OH HO-C-H CH₂OH CH ₂ OH CH₂OH CA) (B) (D) (E) Both choices (B) and (C) could be the correct structure of D-erythrose. CHO H₂C-OH HC OH CH ₂ OH ctrl MAND optionarrow_forwardGive the products of periodic acid oxidation of each of the following. How many moles of reagent will be consumed per mole of substrate in each case? (a) d-Arabinose (b) d-Ribose (c) Methyl β-d-glucopyranosidearrow_forward
- Organic ChemistryChemistryISBN:9781305580350Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. FootePublisher:Cengage LearningOrganic Chemistry: A Guided InquiryChemistryISBN:9780618974122Author:Andrei StraumanisPublisher:Cengage Learning
- Macroscale and Microscale Organic ExperimentsChemistryISBN:9781305577190Author:Kenneth L. Williamson, Katherine M. MastersPublisher:Brooks Cole