Essential Organic Chemistry, Global Edition
3rd Edition
ISBN: 9781292089034
Author: Paula Yurkanis Bruice
Publisher: PEARSON
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Chapter 16, Problem 25P
Interpretation Introduction
Interpretation:
The method to determine which bottle contains D-lyxose is to be stated.
Concept Introduction:
Dilute nitric acid is a strong oxidizing agent. It is used to oxidize
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To 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?
Identify the sugar in each description. a. An aldopentose that is not d-arabinose forms d-arabinitol when it is reduced with NaBH4. b. A sugar that is not D-altrose forms d-altraric acid when it is oxidized with nitric acid. c. A ketose that, when reduced with NaBH4, forms d-altritol and d-allitol.
26. This compound is L-glyceraldehyde. Draw a stereochemically correct representation of C-1
and C-2 of D-glucose.
CHO
|
HO—C—H
|
CH2OH
27. Categorize each of the following as an aldose, a ketose, or neither.
28. Define each in 20 words or less:
(a) anomeric carbon;
(b) enantiomers;
(c) furanose and pyranose;
(d) glycoside;
(e) aldose and ketose.
29. 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?
30. A) Define "reducing sugar." (b) Sucrose is a disaccharide composed of glucose and fructose
(Glc(1 → 2)Fru). Explain why sucrose is not a reducing sugar, even though both glucose
and fructose are.
Chapter 16 Solutions
Essential Organic Chemistry, Global Edition
Ch. 16.1 - Prob. 1PCh. 16.2 - Prob. 2PCh. 16.3 - Prob. 3PCh. 16.3 - Prob. 4PCh. 16.4 - Prob. 5PCh. 16.4 - Prob. 6PCh. 16.5 - Prob. 7PCh. 16.5 - Prob. 8PCh. 16.6 - Prob. 10PCh. 16.8 - Prob. 12P
Ch. 16.8 - Prob. 14PCh. 16.9 - Prob. 15PCh. 16.10 - Prob. 16PCh. 16.11 - Refer to Figure 16.4 to answer the following...Ch. 16 - Prob. 18PCh. 16 - Prob. 19PCh. 16 - Prob. 20PCh. 16 - Prob. 21PCh. 16 - Prob. 22PCh. 16 - Prob. 23PCh. 16 - Prob. 24PCh. 16 - Prob. 25PCh. 16 - Name the following compounds:Ch. 16 - Prob. 28PCh. 16 - Prob. 29PCh. 16 - Prob. 31PCh. 16 - Prob. 32PCh. 16 - Prob. 33PCh. 16 - Prob. 34PCh. 16 - Prob. 35PCh. 16 - Prob. 36PCh. 16 - Prob. 37PCh. 16 - Draw the mechanism for the acid-catalyzed...Ch. 16 - Prob. 39PCh. 16 - Prob. 40PCh. 16 - Prob. 41P
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- From the choices given below select the aldohexose that yields the same alditol as D-idose upon reduction with NaBH 4. Select ALL monosaccharides that satisfy the requirement, excluding the structure referenced in the question. Note that only D structures are shown. To select an L structure click on the name. If no selection exists, then select the referenced structure. H H- H H- CHO OH HO- -OH -OH -OH H CH₂OH D-Allose L-Allose H- CHO -H H -OH HO H H HOH -OH CH₂OH D-Altrose L-Altrose CHO -OH -H -OH H -OH H CH₂OH D-Glucose HO HO- L-Glucose CHO H H OH HO H -OH CH₂OH D-Mannose H L-Mannose CHO OH OH -H L-Gulose OH CH₂OH D-Gulose HO- H HO- H- CHO H- OH HO- -H HO -OH H L-Idose -H CH₂OH D-Idose CHO OH -H CH₂OH D-Galactose HO- -H HO- OH H- L-Galactose HO- CHO H H -H -OH CH₂OH D-Talose L-Talosearrow_forwardFrom the choices given below select the L-aldopentose that yields an optically inactive alditol upon reduction with NaBH4. Select ALL monosaccharides that satisfy the requirement, excluding the structure referenced in the question. Note that only D structures are shown. To select an L structure click on the name. If no selection exists, then select the referenced structure. H H H CHO -OH -OH +OH CH₂OH D-Ribose L-Ribose HO- H H- CHO H OH -OH CH₂OH D-Arabinose L-Arabinose H HO H CHO OH -H -OH CH₂OH D-Xylose L-Xylose HO HO- H- CHO -H H -OH CH₂OH D-Lyxose L-Lyxosearrow_forward4. Draw the structures for the oxidation of the following carbohydrates. a) C-H 主 H CH CHOH erythrose b) [0] Ho CHOH glicese 5. Draw the structures for the reduction of the following carbohydrates. Ho CHOH Cat. C=0 + Hz It. OH CHOH olwollol enythrulse b) Cat. Ho CHCH gucosearrow_forward
- m) Which pyranose ring (A, B, C, or D) in the tetrasaccharide below is derived from D-altrose? The Fischer projections for the four aldohexoses that make up this tetrasaccharide are shown below. B C D HOH CHO CHO CHO CHO HO+H HTOH Fонно н HOH HOH H-OH H-OH H-+-OH H-TOHHOH HOH H+OH HOHнтон нон CHOH CHOH CHOH CHOH De D-glue Dalose Datrone i NH Į HOH STEP 1 OH, HO- answer 1. Just add arrows and charges for steps 1, 2, and 3 in formation of this enamine з no arrows needed here OH н Н ЮН -OH STEP 3 :ÖH н H STEP 2 на это про за почarrow_forwardFrom the choices given below select the aldohexose that yields the same alditol as D-allose upon reduction with NaBH4. Select ALL monosaccharides that satisfy the requirement, excluding the structure referenced in the question. Note that only D structures are shown. To select an L structure click on the name. If no selection exists, then select the referenced structure. H H H H CHO OH HO- -OH H OH H -OH CH₂OH D-Allose L-Allose H CHO -H OH HO- -OH H OH CH₂OH D-Altrose L-Altrose H H CHO OH -OH -OH CH₂OH D-Glucose L-Glucose HO HO H H CHO -H CH₂OH D-Mannose H -H -OH HO- -OH H L-Mannose CHO HOH OH -H -OH CH₂OH D-Gulose L-Gulose HO- H HO- H- CHO -H -OH HO -H HO- +OH H CH₂OH D-Idose H L-Idose CHO OH -H -H -OH CH₂OH D-Galactose L-Galactose HO HO HO H CHO H -H H -OH CH₂OH D-Talose L-Talosearrow_forwardWhich 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.arrow_forward
- C. Trehalose and maltose are both dimers of glucose. However, they have considereably different reactivities. Concisely explain why these differences are observed. HO НО НО HO Но HO OH Он HO OHOH Но trehalose maltose 1. Malthose is a reducing sugar while trehalose is not. 2. Trehalose is very resistant to acid hydrolysis while maltose can be acid-hydrolyzed with ease.arrow_forward(g) Using appropriate prefixes/infixes/suffixes (ketohentese, aldahentase, etc.), classify each of the monosaccharides shown below. СНО CH2OH O: HOI но ОН OH HO H. CH2OH CH2OH I II (h) Identify B-D-altrose and oa-D-altrose from the monosaccharides shown below. CH2OH CH2OH CH2OH CH2OH O. ОН OH OH OH OH OH ОН OH OH OH ОН OH OH OH OH OH I II III IV | (i) Identify B-D-altrose and oa-D-altrose from the monosaccharides shown below. VI I CH2OH CH2OH II V OH III ОН IV H OH Harrow_forwardCHEM 111 WA #3 0 pts Name 1. Draw the structure of a-D-fructose and ß-D-galactose.arrow_forward
- 11. Decide whether the disaccharide shown below is (a) a reducing or non-reducing sugar, (b) a B- sugar or an a-sugar, and (c) contains an a-1,4-glycosidic bond, a B-1,4-glycosidic bond, an a-1,6- glycosidic bond, or a B-1,6-glycosidic bond. CH2OH HO HO CH2 HO HO. HO OHarrow_forwardedu.co D- and L- designations are used to distinguish between the two possible enantiomers of the monosaccharide, galactose. From the Fischer projection, determine the designation of this monosaccharide. H H— HO HO H- =0 c= -OH —H -H Question 8 of 20 OH CH₂OH A) D B) L C) D, L Submit D) This monosaccharide contains no chiral centers. : +arrow_forwardmd 26) What carbon (position) is used to make a glycosidic bond? 27) Draw a-D-maltose (a disaccharide composed of two a-D-glucose monosaccharides in an a- 1,4-glycosidic bond). 28) Draw B-D-lactose (a disaccharide composed of B-D-galactose and B-D-glucose in a B-1,4- glycosidic bond). *29) Draw an equation for the hydrolysis of a-D-maltose. (Will be reviewed in lab.) CHM60 Lecture Worksheet: Carbohydrates 6 10arrow_forward
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