PKG ORGANIC CHEMISTRY
5th Edition
ISBN: 9781259963667
Author: SMITH
Publisher: MCG
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Textbook Question
Chapter 28, Problem 28.43P
Draw a Haworth projection for each compound using the structures in Figures
a.
b.
c.
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12
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
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 28 Solutions
PKG 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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- 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(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_forwardGuar 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 marrow_forwarda. Draw a glycerophospholipid with 16:1n-7 and 18:3n-3 fatty acids esterified to C1 and C2, respectively. Include choline in the head group. b. What are the systematic names and A symbols for the above fatty acids? c. What is the full name of the glycerophospholipid (using the common names)?arrow_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_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_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_forward
- Draw the alpha and beta anomer for D- Glucosearrow_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_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_forward
- Which 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_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_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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