EBK ORGANIC CHEMISTRY
6th Edition
ISBN: 9781260475685
Author: SMITH
Publisher: MCGRAW-HILL HIGHER EDUCATION
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Textbook Question
Chapter 26, Problem 42P
Draw a Haworth projection for each compound using the structures in Figures
a.
b.
c.
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1. Draw the Fischer projections for D-galactose and D-fructose. Identify all functional
groups in each structure.
2. Draw the Haworth projections for
a. B-D-galactose
b. a-D-glucose
Guar gum is a complex polysaccharide used by the food industry
as a stabilizer in salad dressings, ice cream and cream cheese.
HO
HO-
OH
linkage A
sugar chain
HO-
11
OH OH
0.
HO
n
HO
sugar off the chain
OH
o
O
linkage B
HO- OH
HO-
O a. Linkage A is 1,5 a glycosidic linkage
O b. Linkage A is 1,4 a glycosidic linkage
O c.
Linkage A is 1,5 ß glycosidic linkage
O d.
Linkage A is 1,4 ß glycosidic linkage
of
m
1. Write Haworth projection formulas for such substances:
4.1 B-D-glucofuranose;
4.2 a-D-fructopyranose;
4.3 saccharose.
1.4 In the formulas a and b show the hemi-acetal hydroxyl.
2. Write: why lactose is a reducing disaccharide.
3. Write the equations of reactions:
3.1 glucose +Cu(OH):(heat)→;
3.2 glucose +HNO,→;
3.3 и-D-glucopyranose +CH,1—;
3.4 a-D-glucopyranose +(CH,CO),O→;
3.5 lactose hydrolysis;
3.6 glucuronic acid formation from glucose.
4. Describe the signs of reactions:
4.1 iodine starch reaction;
4.2 Selivanov's reactions for the fructose;
4.3 glucose reactions with Cu(OH), with heating.
Chapter 26 Solutions
EBK ORGANIC CHEMISTRY
Ch. 26.2 - Prob. 1PCh. 26.2 - Prob. 2PCh. 26.2 - Label each stereogenic center as R or S. a. b. c....Ch. 26.2 - Convert the ball-and-stick model to a Fischer...Ch. 26.2 - Prob. 5PCh. 26.2 - Prob. 6PCh. 26.3 - Prob. 7PCh. 26.3 - Prob. 8PCh. 26.4 - Prob. 9PCh. 26.4 - Prob. 10P
Ch. 26.6 - Prob. 11PCh. 26.6 - Prob. 12PCh. 26.6 - Prob. 13PCh. 26.6 - Prob. 14PCh. 26.6 - Prob. 15PCh. 26.7 - Prob. 16PCh. 26.7 - Draw a stepwise mechanism for the following...Ch. 26.7 - Prob. 18PCh. 26.8 - Prob. 19PCh. 26.9 - Prob. 20PCh. 26.9 - Prob. 21PCh. 26.9 - Draw the products formed when D-arabinose is...Ch. 26.9 - Prob. 23PCh. 26.10 - Prob. 24PCh. 26.10 - Prob. 25PCh. 26.10 - Prob. 26PCh. 26.10 - Prob. 27PCh. 26.11 - Prob. 28PCh. 26.11 - Prob. 29PCh. 26.12 - Prob. 30PCh. 26.12 - Prob. 31PCh. 26.13 - Prob. 32PCh. 26.13 - Prob. 33PCh. 26.13 - Problem-28.35
Draw the structures of the...Ch. 26.13 - Prob. 35PCh. 26 - 28.37 Convert each ball-and-stick model to a...Ch. 26 - Prob. 37PCh. 26 - Prob. 38PCh. 26 - 28.40 Convert each compound to a Fischer...Ch. 26 - Prob. 40PCh. 26 - Prob. 41PCh. 26 - 28.43 Draw a Haworth projection for each compound...Ch. 26 - Prob. 43PCh. 26 - 28.45 Draw both pyranose anomers of each...Ch. 26 - Prob. 45PCh. 26 - 28.50 Draw the products formed when D-altrose is...Ch. 26 - 28.58 Draw a stepwise mechanism for the following...Ch. 26 - Prob. 62PCh. 26 - Prob. 63PCh. 26 - Prob. 64PCh. 26 - Prob. 65PCh. 26 - Prob. 66PCh. 26 - Prob. 67PCh. 26 - Prob. 68PCh. 26 - Prob. 69PCh. 26 - Prob. 70P
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- CHO 29. но- CH,OH The diagram above depicts a a. Fischer projection b. Haworth structure C. chiral carbon d. more than one choice is correctarrow_forward1. Write Haworth projection formulas for such substances: 4.1 B-D-glucofuranose; 4.2 a-D-fructopyranose; 4.3 saccharose. 1.4 In the formulas a and b show the hemi-acetal hydroxyl. 2. Write: why lactose is a reducing disaccharide. 3. Write the equations of reactions: 3.1 glucose +Cu(ОН),(heat) —; 3.2 glucose +HNO,→; 3.3 a-D-glucopyranose +CH,I→; 3.4 a-D-glucopyranose +(CH;CO);O→; 3.5 lactose hydrolysis; 3.6 glucuronic acid formation from glucose. 4. Describe the signs of reactions: 4.1 iodine starch reaction; 4.2 Selivanov's reactions for the fructose; 4.3 glucose reactions with Cu(OH); with heating.arrow_forward1. Draw L-Glucose in the Fisher projection and Haworth diagram 2. Connect D-glucose and D-fructose using an alpha 1,4-glycosidic bondarrow_forward
- 4. What is the polysaccharide that contains glucose units with a(1- 4) glycosidic bonds and branches a(16) glycosidic bonds every 12 units? 5. What is the polysaccharide that contains glucose units with only a(1→4) glycosidic bonds?arrow_forwardWhich of the following has the highest iodine number? A. 1-oleyl-2-arachidonyl-3-palmitoyl glyceride B. 1-lauroyl-2,3-di-linolenyl glyceride C. 1-myritoleyl-2-stearoyl-3-linoleyl glyceride D. 1-palmitoleyl-2,3-arachidoyl glyceride E. 1,2,3-tri-oleyl glyceridearrow_forwardWhich of the following glycosidic linkage is found in maltose? * A. Glucose (a1-2B) Fructose B. Glucose (a1-4) Glucose C. Galactose (B1-4) Glucose D. Glucose (B1-4)Glucosearrow_forward
- 5. Match the following: A. A triglyceride on hydrolysis gives, 1. Sphingosine Fatty +Carbohydrate 2. A non-saponifiable lipid B. A wax consists of, C. Phosphoglyceride consists of, 3. Sphingosine Fatty acid + Phosphoric acid+ Carbohydrate 4. A set of 3 6-membered And a 5-membered ring Fused together. 5. Saponifiable lipid. D. A sphingomyelin consists of, E. A glycolipid consists of, F. A steroid is a special type of ring system Consists of 6. Fatty acids and long Chain alcohols 7. Glycerol, Fatty acids+ Phosphoric acids G. A prostaglandin is an example of, H. Triglycerides, phospholipids and glycol Lipids are examples of 8. Fatty acids + Glycerolarrow_forwardIdentify the major class of each lipid from its components. a. fatty acids + glycerol b. fatty acids + sphingosine + a carbohydrate c. fatty acids + high-molecular-weight alcohols other than glycerol d. glycerol + fatty acids + phosphate group + choline e. fatty acids + sphingosine + phosphate group + a nitrogen compoundarrow_forwardShown below is an oligosaccharide. Mark each of the statements about this oligosaccharide as true (T) or false (F). ت تا OH OH он он OH он но но но- NHAC он он но он NHAC он он Contains a pentose f. Contains a uronic acid a. b. Contains a 1,3 glycosidic link g. Can mutorotate Contains glucose h. Is a branched chain sugar C. d. Contains galactose i. Is a form of starch е. Contains a deoxy sugar j. Contains an oa anomeric carbonarrow_forward
- md 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_forwardWhich pairs of molecules are interconvertible via mutarotation? O a. D-glucose and D-fructose O b. D-glucose and D-galactose O c. D-glucose and D-glucosamine O d. a-D-glucose and B-D-glucosearrow_forwardAnswer the following questions about monosaccharide B.a. Draw the β anomer of B in a Haworth projection.b. Draw the α anomer of B in a three-dimensional representation using a chair conformation.c. What products are formed when B undergoes the Kiliani–Fischer synthesis?d. What product is formed when B is treated with NaBH4 in CH3OH?e. Draw the disaccharide formed when two molecules of B are joined by a 1→4-β-glycosidic linkage.arrow_forward
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