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Interpretation:
From the cyclic structure of allose given, whether it is i) a furanose or pyranose form ii) α- or β- anomer iii) D or L sugar are to be stated.
Concept introduction:
The pyranose form is a cyclic hemiacetal form with a six membered ring formed by the nucleophilic addition of the –OH group on C5 to the C1 carbonyl group. The furanose form is a cyclic hemiacetal form with a five membered ring formed by the nucleophilic addition of the –OH group on C5 to the C2 carbonyl group.
The orientation of –OH group differs in α- and β- anomers. In α- anomer the OH on C1 is cis to the –OH at the lowest chirality center in Fischer projection, while in β- anomer the –OH on C1 is trans to the –OH at the lowest chirality center in Fischer projection.
D sugars have the –O- at C5 on the right in the uncoiled form while L sugars have -O- at C5 on the left.
To state:
From the cyclic structure of allose given, whether it is i) a furanose or pyranose form ii) α- or β- anomer iii) D or L sugar.
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Chapter 25 Solutions
Organic Chemistry
- Xylulose has the following structural formula. To what carbohydrate class does xylulose belong based on the number of carbons and carbonyl functionality? A) aldotetrose B) aldopentose C) ketotetrose D) ketopentose E) ketohexosearrow_forwardLactose is a disaccharide in which a glycosidic linkage connects the monosaccharides galactose and glucose. OH НО OH (a) Identify the glycosidic linkage and the acetal carbon in lactose. (b) What type of glycosidic linkage does lactose have (i.e., is it 1,1'-, 1,2'-, etc., and is it a or B)? (c) People who are lactose intolerant are deficient in the enzyme lactase, and therefore cannot efficiently break down the disaccharide into its monosaccharides. When lactose is treated with aqueous acid, however, this hydrolysis can take place, though relatively slowly. Draw the complete, detailed mechanism and the products of the acid-catalyzed hydrolysis of lactose. Но ОН НО ОН ОН Lactosearrow_forwardThe most stable conformation of the pyranose ring of most D-aldohexoses places the largest group, CH2OH, in the equatorial position. An exception to this is the aldohexose D-idose. Draw the two possible chair conformations of either the a or ß anomer of D-idose. Explain why the more stable conformation has the CH2OH group in the axial position.arrow_forward
- (d) Use the diagram below to complete the cyclic alpha form of structure V (e) Circle the hemiacetal in cyclic alpha form of structure V. (f) Redraw the cyclic alpha form of structure V but replace the OH group on the anomericcarbon with a methoxy group. Is this modified monosaccharide a reducing sugar or anonreducing sugar?arrow_forward(g) Using appropriate prefixes/infixes/suffixes (ketoheptose, aldoheptose, etc.), classify each of the monosaccharides shown below. CHO CH2OH Но IH но- HO- HO- HO H. CH2OH CH2OH I II (h) Identify B-D-altrose and a-D-altrose from the monosaccharides shown below. CH2OH CH2OH CH2OH CH2OH OH OH OH ОН OH ОН ОН OH OH OH OH OH OH OH OH OH I II II IV (i) Identify B-D-altrose and a-D-altrose from the monosaccharides shown below. VI I CH2OH O CH2OH II H V ОН, III IV OH OH Harrow_forwardChemistry the two sugars are aldo/keto hexos/pentos that has been ciclised to a fur/pyr anose. They are alfa/beta-anmore and are what kind of sugars CH2OH CH₂OH OH OH OH OH OH OH OHarrow_forward
- Classify the following monosaccharides as an aldose or ketose. I need help on number 5, a-d.arrow_forward(h) Identify B-D-altrose and a-D-altrose from the monosaccharides shown below. VI I CH2OH O. CH2OH II H V ОН, IV H III OH OH H (i) The monosaccharide below is a(n) (d-aldopentose, R-aldopentose, S- aldopentose, L-aldopentose, D-aldopentose).arrow_forwardTrehalose and maltose are both dimers of glucose. However, they have considereably different reactivities. Concisely explain why these differences are observed. но но HO HO но "HO он но он OH O HO OHOH но trehalose maltose 1. Malthose is a reducing sugar while trehalose is not. 2. Trehalose is very resistant to acid hydrolysis while maltose can be acid-hydrolyzed with ease.arrow_forward
- 2. Draw the two aldohexoses and one ketohexose that can be derived from the enol shown below. HC OH но H- HO- HO ČH,OH 3. Classify the following monosaccharides as reducing and nonreducing sugars. CH,OH CH,OH CH,OH OH он но - HO- OH OH HO он OH OH ČH,OH II III 4. Identify and name the glycosidic bond in the structure shown below. CH,OH OH OH онarrow_forwardThe structure of 4 isomers of an aldotetrose carbohydrate are given. 1) select every structure that is a diastereomer of structure D A, B, or C? 2) select every structure that is a enantiomer of structure C D, B, or A? 3) select every structure that is a stereoisomer of structure D A, B, or Carrow_forwardDraw the isomers for each aldotetrose and ketopentose in the figure below and designate each isomer as a D or L sugar and designate also the R and S in every chiral centers. Label the enantiomers and diastereomers respectively. CH,OH C=0 Н—С—ОН Н-С—ОН Н—С—ОН H-C-OH ČH,OH ČH,OHarrow_forward
- Introduction to General, Organic and BiochemistryChemistryISBN:9781285869759Author:Frederick A. Bettelheim, William H. Brown, Mary K. Campbell, Shawn O. Farrell, Omar TorresPublisher:Cengage LearningOrganic ChemistryChemistryISBN:9781305580350Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. FootePublisher:Cengage Learning
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