Organic Chemistry
5th Edition
ISBN: 9780078021558
Author: Janice Gorzynski Smith Dr.
Publisher: McGraw-Hill Education
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Question
Chapter 28, Problem 28.8P
Interpretation Introduction
Interpretation: Two possible epimers of D-erythrose are to be drawn and their name is to be stated.
Concept introduction: Two compounds which are neither superimposable nor mirror images to each other and the configuration of one of their stereogenic centers is different are known as epimers.
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Which of the following is FALSE?
a.
D-altrose and D-talose have the same osazones.
b.
D-glucose and D-galactose have different osazones.
c.
Trioses and tetroses cannot form the furfural derivatives because of their inability to form the 5-membered ring.
d.
Barfoed’s reagent, a weaker oxidizing agent than Benedict’s reagent, can only oxidize monosaccharides.
Draw a diastereomers of D- Glucose
Starting with a Fischer projection of D-fructose, write equations showing the formation of α-Dfructopyranose, α-Dfructofuranose, β-D-fructopyranose, and β-D-fructofuranose
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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- show the glycosidic linkage of b-D-galactose and b-D-galactose (show drawing)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_forwardDraw the following compounds: Cellobiose: 2 glucose β-1,4arrow_forward
- Fructose in its bβ - D - pyranose form accounts for the powerful sweetness of honey. The β - D - furanose form, although sweet, is not as sweet as the pyranose form. The furanose form is the more stable form. Draw the two forms and explain why it may not always be wise to cook with honey.arrow_forwardTo synthesize D-galactose, a student went to the stockroom to get some D-lyxose to use as a starting material. She found that the labels had fallen off the bottles containing D-lyxose and D-xylose. How can she determine which bottle contains D-lyxose?arrow_forwardDraw two possible epimers of D-erythrose. Name each of these compounds using self drawn figure ?arrow_forward
- starting with a fischer projection of d-fructose write questions showing the formation of a D fructopyranose, a D-frutoranose, and B-D fructoruranosearrow_forwardDraw the structure of the disaccharide maltose (-D-glucopyranosyl (1→4)-D-glucopyranose). Indicate with arrows the reducing end and the acetal functional group.arrow_forwarda) Draw Haworth projections of both - and -anomers of D-fructose. Indicate which carbon is the anomeric carbon.b) Sucrose is a disaccharide made up of a molecule of D-fructose and D-glucose. Draw the structure of sucrose clearly indicating the linkage between the two monosaccharides and its biological significance.c) Tollen’s reagent is a very mild oxidizing agent which normally oxidize aldehydes but not ketones. However, both glucose and fructose give positive results with Tollen’s reagent and are classified as reducing sugars. Explain how fructose can also give positive results with Tollen’s reagent (illustrate using structures).arrow_forward
- Name an aldohexose other than d-glucose that is oxidized to d-glucaric acid by nitric acid.arrow_forwardDraw two possible epimers of D-erythrose. Name each of these compounds using Figure 28.4.Figure 28.4: The family of D-aldoses having three to six carbon atomsarrow_forwardName an aldohexose other than d-glucose that is oxidized to d-glucaric acid by nitric acid. a. What is another name for d-glucaric acid? b. Name another pair of aldohexoses that are oxidized to identical aldaric acids.arrow_forward
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