Organic Chemistry
4th Edition
ISBN: 9780073402772
Author: Janice G. Smith
Publisher: MCG
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Chapter 28, Problem 28.49P
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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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.
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
Lactose contains what number of anomeric carbons and what number of glycosidic bonds:
CH2OH
ОН
CH2OH
ОН
OH
OH
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 - Draw a stepwise mechanism for the following...Ch. 28 - Prob. 28.18PCh. 28 - Prob. 28.19PCh. 28 - Prob. 28.20PCh. 28 - Prob. 28.21PCh. 28 - Draw the products formed when D-arabinose is...Ch. 28 - Prob. 28.23PCh. 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 - Convert each compound to a Fischer projection and...Ch. 28 - Prob. 28.41PCh. 28 - Prob. 28.42PCh. 28 - Prob. 28.43PCh. 28 - Prob. 28.44PCh. 28 - Prob. 28.45PCh. 28 - Draw both pyranose anomers of each aldohexose...Ch. 28 - Prob. 28.47PCh. 28 - Prob. 28.48PCh. 28 - Prob. 28.49PCh. 28 - Prob. 28.50PCh. 28 - Prob. 28.51PCh. 28 - Prob. 28.52PCh. 28 - Prob. 28.53PCh. 28 - What products are formed when each compound is...Ch. 28 - Prob. 28.55PCh. 28 - Prob. 28.56PCh. 28 - Prob. 28.57PCh. 28 - Prob. 28.58PCh. 28 - 28.58 Draw a stepwise mechanism for the following...Ch. 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 - Prob. 28.71PCh. 28 - Prob. 28.72PCh. 28 - Prob. 28.73PCh. 28 - Prob. 28.74PCh. 28 - Prob. 28.75PCh. 28 - Prob. 28.76PCh. 28 - Prob. 28.77PCh. 28 - Draw a stepwise mechanism for the following...Ch. 28 - Prob. 28.79P
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- Name the two monosaccharide units of which trehalose is composedarrow_forwardDescribe each glycosidic bond in this trisaccharide.arrow_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_forward
- The following is the structure of salicin, a bitter-tasting compound found in the bark of willow trees: The aromatic ring portion of this structure is quite insoluble in water. How would forming a glycosidic bond between the aromatic ring and β - D -glucose alter the solubility?arrow_forwardConsider the following compound, which is used by insects and some fungi to store energy: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_forwardIdentify the type(s) of glycosidic bonds in digitoxin / digoxin.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_forwardCan you please solve this question for me?arrow_forward2. 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_forward
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