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ORGANIC CHEMISTRY
5th Edition
ISBN: 9781259977596
Author: SMITH
Publisher: MCG
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Chapter 28, Problem 28.48P
Interpretation Introduction
Interpretation: The two possible chair conformations of either
Concept introduction: An idose is a monosaccharide which contains six carbon atoms and an
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Students have asked these similar questions
The 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.
The 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 α or β anomer of D-idose. Explain why the more stable conformation has the CH2OH group in the axial position.
Draw 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,OH
Chapter 28 Solutions
ORGANIC CHEMISTRY
Ch. 28 - Prob. 28.1PCh. 28 - Prob. 28.2PCh. 28 - Label each stereogenic center as R or S. a. b. c....Ch. 28 - Convert the ball-and-stick model to a Fischer...Ch. 28 - Prob. 28.5PCh. 28 - Prob. 28.6PCh. 28 - Prob. 28.7PCh. 28 - Prob. 28.8PCh. 28 - Prob. 28.9PCh. 28 - Prob. 28.10P
Ch. 28 - Prob. 28.11PCh. 28 - Prob. 28.12PCh. 28 - Prob. 28.13PCh. 28 - Prob. 28.14PCh. 28 - Prob. 28.15PCh. 28 - Prob. 28.16PCh. 28 - Prob. 28.17PCh. 28 - Draw a stepwise mechanism for the following...Ch. 28 - Prob. 28.19PCh. 28 - Prob. 28.20PCh. 28 - Prob. 28.21PCh. 28 - Prob. 28.22PCh. 28 - Draw the products formed when D-arabinose is...Ch. 28 - Prob. 28.24PCh. 28 - Prob. 28.25PCh. 28 - Prob. 28.26PCh. 28 - Prob. 28.27PCh. 28 - Prob. 28.28PCh. 28 - Prob. 28.29PCh. 28 - Prob. 28.30PCh. 28 - Prob. 28.31PCh. 28 - Prob. 28.32PCh. 28 - Prob. 28.33PCh. 28 - Prob. 28.34PCh. 28 - Problem-28.35
Draw the structures of the...Ch. 28 - Prob. 28.36PCh. 28 - 28.37 Convert each ball-and-stick model to a...Ch. 28 - Prob. 28.38PCh. 28 - Prob. 28.39PCh. 28 - 28.40 Convert each compound to a Fischer...Ch. 28 - Prob. 28.41PCh. 28 - Prob. 28.42PCh. 28 - 28.43 Draw a Haworth projection for each compound...Ch. 28 - Prob. 28.44PCh. 28 - 28.45 Draw both pyranose anomers of each...Ch. 28 - Prob. 28.46PCh. 28 - Prob. 28.47PCh. 28 - Prob. 28.48PCh. 28 - Prob. 28.49PCh. 28 - 28.50 Draw the products formed when D-altrose is...Ch. 28 - Prob. 28.51PCh. 28 - Prob. 28.52PCh. 28 - Prob. 28.53PCh. 28 - Prob. 28.54PCh. 28 - Prob. 28.55PCh. 28 - Prob. 28.56PCh. 28 - Prob. 28.57PCh. 28 - 28.58 Draw a stepwise mechanism for the following...Ch. 28 - Prob. 28.59PCh. 28 - Prob. 28.60PCh. 28 - Prob. 28.61PCh. 28 - Prob. 28.62PCh. 28 - Prob. 28.63PCh. 28 - Prob. 28.64PCh. 28 - Prob. 28.65PCh. 28 - Prob. 28.66PCh. 28 - Prob. 28.67PCh. 28 - Prob. 28.68PCh. 28 - Prob. 28.69PCh. 28 - Prob. 28.70PCh. 28 - 28.71 Draw a stepwise mechanism for the following...
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- Lactose contains what number of anomeric carbons and what number of glycosidic bonds: CH2OH ОН CH2OH ОН OH OH OHarrow_forwardOH НО HO OH НО Но OH ОН ОН OH What are the monosachharides that make up this trisaccharide? O a-D-glucopyranose, a-D-galactopyranose, a-D-fructofuranose a-D-glucopyranose, a-D-galactopyranose, B-D-fructofuranose a-D-glucopyranose, a-D-glucopyranose, B-D-fructofuranose a-D-galactopyranose, a-D-glucopyranose, a -D-fructofuranosearrow_forwardWhich characteristic is shared by the ring forms of the given monosaccharides? * CH2OH CHO O= H- HO- HO- но- H- но- Но H H- -OH ČH,OH ČH2OH Both exist mainly as furanoses. Both contain a hemiacetal bond. Both can undergo mutarotation. O Both exist mainly as pyranoses.arrow_forward
- The structures of 4 isomers of ketopentose are shown. 1) which of the structures are diastereomers of structure A? C, B, or D 2) which of the structures are enantiomers of structure C? B, A, or D 3) which of the structures are stereoisomers of strcuture A?C, D, or Barrow_forwardThe 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 .arrow_forwardWhich of the following is the correct pair of monosaccharides needed 2 to form the given glycoside? * CH2OH CH-OH CH2OH OH он он OH OH a-D-fructofuranose & B-D-glucopyranose a-D-sorbofuranose & B-D-allopyranose a-D-mannofuranose & B-D-glucopyranose O a-D-sorbofuranose & B-D-galactopyranosearrow_forward
- Identify the anomeric carbon. Identify the glycosidic linkage. Lactose ОН ОН OH HO HO, HO OHarrow_forwardClassify each monosaccharide according to the position of the carbonyl group and the number of carbon atoms in the molecule. CHO CH₂OH OH H -OH CH,OH aldotriose aldotetrose aldopentose ketotetrose ketotriose ketopentose galactose ketopentose aldotetrose ketotetrose ketohexose aldohexose aldopentose OH OH aldotetrose aldopentose ketohexose aldohexose ketopentose ketotetrosearrow_forwardWhen a pyranose is in the chair conformation in which the CH2OH group and the C-1 OH group are both in axial positions, the two groups can react to form an acetal. This is called the anhydro form of the sugar (it has “lost water”). The anhydro form of D-idose is shown here. Explain why about 80% of d-idose exists in the anhydro form in an aqueous solution at 100 °C, but only about 0.1% of D-glucose exists in the anhydro form under the same conditions.arrow_forward
- 2. Sucrose is a disaccharide formed from the condensation of glucose and fructose sugars. Draw the structure of sucrose that results from the condensation reaction between the indicated -OH groups. CH2OH 1, CH,OH он 1. OH но CH,OH OH HO H он OHarrow_forwardWhich disaccharide contains an a(1-4) glycosidic bond? CH2OH CH,OH CH2OH CH2OH OH OH OH OH OH OH ÓH ÓHarrow_forwardClick the "draw structure" button to launch the drawing utility. Convert the cyclic form to an acyclic monosaccharide. CH₂OH O- H H OH HO H H OH draw structure 1b)Use a simple model to convert the following Fischer projection to a line structure showing stereochemistry Br OHC CH3 HO–|CH,CH3 H S d ww b Harrow_forward
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