Essential Organic Chemistry (3rd Edition)
3rd Edition
ISBN: 9780321937711
Author: Paula Yurkanis Bruice
Publisher: PEARSON
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Chapter 20.2, Problem 4P
Draw the structure of an optically active fat that, when hydrolyzed, gives the same products as the fat in Problem 3.
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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.
1. Bromine test is a test used to determine the degree of unsaturation in fatty acids. A colorless solution indicates a positive result. Which of the following fatty acids will not give a colorless solution?
oleic acid
Linoleic acid
Lauric acid
Linolenic acid
2. The following can cause the breaking of hydrogen bond, except?
addition of silver nitrate
heating
agitation
addition of acetic acid
none of the above
The tea leaves that contain the caffeine to be isolated are predominantly
composed of cellulose, a natural and extremely abundant polymer of glucose.
Look up the chair structure of B-D-glucose (B-D-glucopyranose, the monomer
from which the cellulose polymer is composed). Draw this structure, draw the
flipped chair, and indicate which conformer you think is more stable, if either.
BRIEFLY explain your choice.
Chapter 20 Solutions
Essential Organic Chemistry (3rd Edition)
Ch. 20.1 - Prob. 1PCh. 20.2 - Prob. 2PCh. 20.2 - Prob. 3PCh. 20.2 - Draw the structure of an optically active fat...Ch. 20.4 - Prob. 6PCh. 20.4 - Prob. 7PCh. 20.4 - The membrane phospholipids in deer have a higher...Ch. 20.4 - Prob. 9PCh. 20.6 - Prob. 10PCh. 20.6 - Prob. 11P
Ch. 20.6 - Prob. 12PCh. 20.7 - Propose a mechanism for the biosynthesis of...Ch. 20.7 - Prob. 14PCh. 20.8 - Draw the individual 1,2-hydride and 1,2-methyl...Ch. 20.9 - Prob. 16PCh. 20 - Prob. 17PCh. 20 - Prob. 18PCh. 20 - Cardiolipins are found in heart muscles. Draw the...Ch. 20 - Prob. 20PCh. 20 - 5-Androstene-3,17-dione is isomerized to...Ch. 20 - Prob. 22PCh. 20 - Prob. 23PCh. 20 - Prob. 24PCh. 20 - Eudesmol is a sesquiterpene found in eucalyptus....
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- Trehalose and maltose are both dimers of glucose. However, they have considereably different reactivities. Concisely explain why these differences are observed. OH но но но OH LOH он O'HO- он OH. OHOH HO 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_forward1. A carbohydrate has the molecular formula C6H12O6 and has three chiral carbons. Is this a ketohexose, an aldohexose, or an aldopentose? Explain2. Show the Fischer projection formula for the organic product of the reaction between D-ribose and warm, dilute nitric acid. Circle the carbons that are oxidized in this reaction.arrow_forwardLinoleic acid is shown below. What makes this fatty acid particularly susceptible to autoxidation? 1. The red CH bond has a low bond dissociation energy because it is doubly allylic. 2. The red CH bond has a high bond dissociation energy because it is doubly allylic. 3. The red CH bond is the most accessible to reaction with O2 because it is the least sterically crowded CH bond. 4. Both 2 and 3.arrow_forward
- Fats can be either optically active or optically inactive, depending on their structure. Draw the structure of an optically active fat that yields 2 equivalents of stearic acid and 1 equivalent of oleic acid on hydrolysis. Draw the structure of an optically inactive fat that yields the same products.arrow_forwardC. Trehalose and isomaltose are both dimers of glucose. However, they have considerably different reactivities. Concisely explain why these differences are observed. OH HO но но. HO HO OH Но- он но OH HO НО trehalose isomaltose 1. Isomaltose is a reducing sugar while trehalose is not. 2. Trehalose is very resistant to acid hydrolysis while isomaltose can be acid-hydrolyzed with ease.arrow_forward3. HO" он HO. но, но HO OH Solanine Solanine is a naturally occurring compound that contain glycoside bonds as part of its structure. Determine the structure of aglycon and monosaccharides fomed when solanine is hydrolyzed with aqueous acid. Include all the appropriate anomers.arrow_forward
- 27. Which of the following statements about cholesterol is not correct? CH3 CH3 H. d но Cholesterol (a) Cholesterol is a steroid that contains a tetracyclic ring system. (b) Cholesterol is a steroid that contains 8 chiral carbons and can form 28 or 256 stereoisomers. (c) Each atom or group attached to a ring-junction carbon (i.e., carbons a -e) is in a trans or axial position. Because of this the tetracyclic ring system is mostly flat. (d) Cholesterol is used to synthesized vitamin D, bile acids, sex hormones, and adrenocorticoid hormones. (e) Cholesterol is not found in the cell membranes of animals.arrow_forwardConsider the following fatty acids: 0 CH₂-(CH₂)2 C -OH Myristic Acid CH₂-(CH₂-CH=CH-CH₂-CH=CH-06- Lindles Acid A) What type of fatty acid is Linoleic Acid (Saturated Monounsaturated or Polyunsaturated)? B) Which fatty acid listed above would have the lower meking point C) Draw the structure of a triacylglycerol that contains tw molecules of file acid and one molecule of myristic acid D) True or False: As the number of carbons in a saturated fatty acid is the melting point decreases. Fals: As the number of double bonds in an unsaturated fatty increases thearrow_forwardIn solution, glucose is mostly found in the cyclic hemiacetal state, which lacks an aldehyde group. How are mild oxidising agents able to oxidise glucose?arrow_forward
- 10. Draw the reaction of Galactose with Benedict solution. Answer the following questions based on these structures. Here is the terminology you can use to describe the relationships. Structural isomers, Enantiomers, Diastereomers, and no relationship. CHO CHO -H H- Н- CHO HO-H OH H- НО- Н- Н- OH OH CH₂OH CHO H H -ОН -ОН но- Н- CH₂OH H -ОН CH2OH 2 Н- Н- но- НО- CHO -ОН -ОН -H -H CH2OH 8 НО Н- H- НО- -ОН -Н CH₂OH 3 CH₂OH 7 11. What is the relationship between 1 and 4? 12. What is the relationship between 1 and 3? 13. What is the relationship between 1 and 5? 14. What is the relationship between 2 and 9? Н- но 15. What is the relationship between 4 and 10? 16. What is the relationship between 5 and 6? ОН 17. What is the relationship between 2 and 10? CH2OH -ОН -Н CH2OH 9 НО- Н- Н- CH2OH :0 -H OH OH CH2OH 4 НО- НО- Н- H- но- но- CH2OH H——OH -Н -Н CH₂OH 10 H H OH OH CH₂OH 5 Н- но- но- Н- CHO -OH -H H -OH CH2OH 6arrow_forwardA reddish color is obtained when compound A (a disaccharide) is reacted with Benedict solution. Is this compound more likely maltose or sucrosearrow_forward2. Which of the sugar solution gave a negative/ positive test with Orcinol reagent? Why? What is the purpose of this test? How are carbohydrates differentiated by this test? What is the reaction involved in this test?arrow_forward
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