Organic Chemistry (9th Edition)
9th Edition
ISBN: 9780321971371
Author: Leroy G. Wade, Jan W. Simek
Publisher: PEARSON
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Chapter 23.9, Problem 23.25P
- a. Show the product that results when fructose is treated with an excess of methyl iodide and silver oxide.
- b. Show what happens when the product of part (a) is hydrolyzed using dilute acid.
- c. What do the results of parts (a) and (b) imply about the hemiacetal structure of fructose?
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1mL of Benedict's reagent is added to 1mL of the test solution.
The mixture is then heated for 5 minutes in water bath.
Appearance of reddish-brown precipitates indicates the presence of a reducing sugar.
Glucose and Fructose give a positive result. Sucrose on the other hand gives a negative result.
Explain why sucrose give a negative result when subjected to a Benedict's test.
Show the product that results when fructose is treated with an excess of methyl iodideand silver oxide
Would you expect fructose or glucose to form a red color rapidly with Seliwanoff’s reagent? Explain your answer.
Chapter 23 Solutions
Organic Chemistry (9th Edition)
Ch. 23.2 - Prob. 23.1PCh. 23.3A - Prob. 23.2PCh. 23.3A - Prob. 23.3PCh. 23.3B - Draw and name the enantiomers of the sugars shown...Ch. 23.3B - Prob. 23.5PCh. 23.3C - Prob. 23.6PCh. 23.4 - Draw the Haworth projection for the cyclic...Ch. 23.4 - Prob. 23.8PCh. 23.4 - Prob. 23.9PCh. 23.4 - Prob. 23.10P
Ch. 23.4 - Prob. 23.11PCh. 23.5 - Prob. 23.12PCh. 23.5 - Prob. 23.13PCh. 23.6 - Prob. 23.14PCh. 23.6 - Prob. 23.15PCh. 23.7 - Prob. 23.16PCh. 23.7 - Prob. 23.17PCh. 23.7 - Two sugars, A and B, are known to be glucose and...Ch. 23.7 - Prob. 23.19PCh. 23.8 - Prob. 23.20PCh. 23.8 - Prob. 23.21PCh. 23.8 - Prob. 23.22PCh. 23.8 - Prob. 23.23PCh. 23.8 - Prob. 23.24PCh. 23.9 - a. Show the product that results when fructose is...Ch. 23.9 - Prob. 23.26PCh. 23.9 - Prob. 23.27PCh. 23.9 - Prob. 23.28PCh. 23.10 - Prob. 23.29PCh. 23.10 - Prob. 23.30PCh. 23.10 - Prob. 23.31PCh. 23.11 - Prob. 23.32PCh. 23.11 - The Wohl degradation, an alternative to the Ruff...Ch. 23.11 - Prob. 23.34PCh. 23.11 - Prob. 23.35PCh. 23.12A - Prob. 23.36PCh. 23.12A - Give an equation to show the reduction of Tollens...Ch. 23.12A - Prob. 23.38PCh. 23.12B - Prob. 23.39PCh. 23.12C - Prob. 23.40PCh. 23.12C - Prob. 23.41PCh. 23.13A - Prob. 23.42PCh. 23.15 - Cytosine, uracil, and guanine have tautomeric...Ch. 23.15 - a. An aliphatic aminoglycoside is relatively...Ch. 23.16C - Prob. 23.45PCh. 23 - Prob. 23.46SPCh. 23 - Prob. 23.47SPCh. 23 - Prob. 23.48SPCh. 23 - Prob. 23.49SPCh. 23 - Prob. 23.50SPCh. 23 - Prob. 23.51SPCh. 23 - Prob. 23.52SPCh. 23 - Prob. 23.53SPCh. 23 - Prob. 23.54SPCh. 23 - Prob. 23.55SPCh. 23 - Prob. 23.56SPCh. 23 - Prob. 23.57SPCh. 23 - Prob. 23.58SPCh. 23 - Prob. 23.59SPCh. 23 - Prob. 23.60SPCh. 23 - Prob. 23.61SPCh. 23 - Prob. 23.62SPCh. 23 - Prob. 23.63SPCh. 23 - Draw the structure of a four-residue segment of...Ch. 23 - Retroviruses like HIV, the pathogen responsible...Ch. 23 - Prob. 23.66SPCh. 23 - Prob. 23.67SP
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- Why is molecule "A" the major acetal formed when d-erythrose reacts with H2SO4 and acetone as opposed to molecule "B"?arrow_forwardWhat is the difference in results for sucrose and hydrolyzed sucrose when reacted with Benedict's reagent?arrow_forwardDraw the products from Killiani-Fischer reaction of D-ribose and L-Xylose.arrow_forward
- Thoroughly explain why (a)malthose is a reducing sugar while trehalose is not based on their structures. (b)Why is trehalose very resistant to acid hydrolysis while maltose can be acid-hydrolyzed with ease. Give clear explanations.arrow_forwardAn important technique for establishing relative configurations among isomeric aldoses and ketoses is to convert both terminal carbon atoms to the same functional group. This can be done either by selective oxidation or reduction. As a specific example, nitric acid oxidation of d-erythrose gives meso-tartaric acid . Similar oxidation of d-threose gives (2S,3S)-tartaric acid. Given this information and the fact that d-erythrose and d-threose are diastereomers, draw Fischer projections for d-erythrose and d-threose. Check your answers against Table 25.1.arrow_forwardA chemist is performing a Fischer Esterification but can't find the sulfuric acid. This reagent is important because itarrow_forward
- On the basis of the results from Benedict’s test, which sugars are reducing? nonreducing?arrow_forwardWhat is a reducing sugar? What other types of sugars besides glucose might you measure using the dinitrosalicylic acid (DNS) reagent?arrow_forward1.Explain what is anomeric effect and why it happens? 2.Explain how a glycosyl acetimidate can loss its glycosyl donor activity?arrow_forward
- d-Altrose is an aldohexose. Ruff degradation of d-altrose gives the same aldopentose asdoes degradation of d-allose, the C3 epimer of glucose. Give the structure of d-altrosearrow_forwardi would like to ask the following questions: 1. Aside from the reagent and the positive results, what is the difference between Fehling’s Test, Moore’s test and Benedict’s Test if they are all used to detect the presence of reducing sugar?2. In Benedict’s Test, why are there different colors? Why not just one color in varying shades?3. Why is sucrose not a reducing sugar even though most disaccharides are reducing sugars?arrow_forwardWhat can be interpreted when the Benedict's test is applied to acid catalyze hydrolyzed sucrose?arrow_forward
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