(a) Is the following stereoisomer of a D or L sugar? (b) In the box provided, draw the enantiomer of the carbohydrate shown. (c) In the box provided, draw the C-2 epimer of the carbohydrate shown. (d) In the box provided, draw a single deoxy sugar of the carbohydrate shown. CHO H. Но -H- HO -H- H CH2OH enantiomer C-2 epimer A deoxy sugar

(a) Is the following stereoisomer of a D or L sugar? (b) In the box provided, draw the enantiomer of the carbohydrate shown. (c) In the box provided, draw the C-2 epimer of the carbohydrate shown. (d) In the box provided, draw a single deoxy sugar of the carbohydrate shown. CHO H. Но -H- HO -H- H CH2OH enantiomer C-2 epimer A deoxy sugar

Organic Chemistry

9th Edition

ISBN:9781305080485

Author:John E. McMurry

Publisher:John E. McMurry

Chapter25: Biomolecules: Carbohydrates

Section25.SE: Something Extra

Problem 44AP

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6 сH-он (5 4 OH 1 2 ОН 3 OH (c) Trace and identify the acetal in the above monosaccharide. (d) Draw the hemiacetal that results from above acetal. (e) Draw the open chain equivalent of the sugar in part (d).
I) Draw a proper Fischer projection for the following molecule. Assign each stereogenic carbon as either (R) or (S) and determine if the molecule is either a (D) or (L)-sugar, is this aldose or ketose? ОН он он ОН
3. Cinnamic acid (shown) reacts with bromine to give a bromination product. (a) Draw all four possible stereoisomers of this reaction as a Fischer projection. Label each molecule as A, B, C, and D. (b) Identify the pairs of enantiomers (c) Identify the pairs of diastereomers (d) Identify which pair corresponds to addition to trans-cinnamic acid. Briefly explain your reasoning. O OH Br₂ CH₂Cl₂
A) Draw the structure of any aldohexose in the pyranose ring form. B) Draw the structure of the anomer of the aldohexose you drew above. C) How many asymmetric carbons (chiral centers) does each of these structures have? D) How many stereoisomers of the aldohexoses you drew are theoretically possible?
5. Provide suitable responses for questions (a) – (). 6 CH2OH 4 OH OH 3 OH (a) What is the relative configuration of the above monosaccharide? (b) Which labeled carbon is the anomeric carbon? (c) Trace and identify the acetal in the above monosaccharide. (d) Draw the hemiacetal that results from above acetal. (e) Draw the open chain equivalent of the sugar in part (d). (f) Classify the monosaccharide below as a D-sugar or an L-sugar. H. OH O. OH CH,OH OH OH
Draw the following monosaccharides, using chair conformations for the pyranoses andHaworth projections for the furanoses.(a) a-d-mannopyranose (C2 epimer of glucose)(b) b-d-galactopyranose (C4 epimer of glucose)(c) b-d-allopyranose (C3 epimer of glucose)(d) a-d-arabinofuranose(e) b-d-ribofuranose (C2 epimer of arabinose)
Provide suitable responses for questions (a) –(j).| 6 CH2OH 4 ОН OH OH 2.
1. For lactose (below), OH OH НО НО OH 0 -ОН ОН OH (A) Circle and label any acetal groups (B) Circle and label any hemiacetal groups (C) Use an arrow to point to any glycoside bonds (D) What is the configuration (o or B) at the anomeric carbon of the "left" (E) Which ring (left or right) is in equilibrium with an open-chain form?
Without referring to the chapter, draw the chair conformations of(a) b-d-mannopyranose (the C2 epimer of glucose).(b) a-d-allopyranose (the C3 epimer of glucose).(c) b-d-galactopyranose (the C4 epimer of glucose)
E For the following Fischer projection: c-oH (a) Determine (R)/(S) configuration at each chiral center; (b) Show all stereoisomers, and based on your assignments from part (a), determine what would be (R) or (S) configuration at all chiral centers; (c) Show all enantiomeric and diastereomeric pairs.
The most stable conformation of the pyranose ring of most Daldohexosesplaces the largest group, CH2OH, in the equatorial position.An exception to this is the aldohexose D-idose. Draw the two possiblechair conformations of either the α or β anomer of D-idose. Explain whythe more stable conformation has the CH2OH group in the axial position .
(a) meso-hexane-3,4-diol, CH3CH2CH(OH)CH(OH)CH2CH3, draw any diastereomers.