General, Organic, and Biological Chemistry - 4th edition
4th Edition
ISBN: 9781259883989
Author: by Janice Smith
Publisher: McGraw-Hill Education
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Question
Chapter 15, Problem 58P
Interpretation Introduction
(a)
Interpretation:
The compound pairs should be classified as either enantiomers or diastereomers.
Concept Introduction:
Stereoisomers are molecules with same molecular formula, same molecular formula and different arrangement of atoms in space and they can be divided into two groups, enantiomers and diastereomers. Enantiomers are isomers which are mirror images of each other. Diastereomers are isomers which are not mirror images of each other.
Interpretation Introduction
(b)
Interpretation:
Constitutional isomer of molecule E should be drawn.
Concept Introduction:
In constitutional isomers molecular formula can be similar, but the
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Students have asked these similar questions
1. Which of the following is not true
to the monosaccharide below?
H.
ОН
но-
-H-
но
ОН
ĆH2OH
O It is the Fischer Projection of D-glucose.
It is an aldohexose having 4 chiral
centers and 24 stereoisomers.
It is has a D-glucose because OH- group
bonded to the highest numbered chiral
C is pointing to the right.
It is a polyhydroxy ketone having 8
enantiomeric pair.
a) Which of the following monosaccharides will react with Tollens' reagent? Circle all that
apply.
СООН
CH2OH
CH2OH
OCH3
но-
H-
O:
OH
но
H-
но—н
OH
ČH2OH
ČH2OH
ÓH
II
III
IV
V
b) Which of the following carbohydrates is sucrose?
OH
OH
OH
но
OH
HO,
O.
OH
"OH
HO
OH
Он
HO
OH
II
I
HO,
HO.
Он
HO,
HO.
HO,
OH
Но
Он
но.
OH
HO,,
HO,
OH
HOl
HO
OH
но
он
III
Он
HO
IV
HO
но
4. Identify the component monosaccharides of each of the following compounds and
describe the type of glycosidic linkage in each.
Но
он
Но
OH
HO
он
Но-
Но-
(a)
OH
(c)
CH,OHO.
(b)
CH2OHO
Lon
OH
HO
H
ČHOH
H
OH
ÓH
ОН
Chapter 15 Solutions
General, Organic, and Biological Chemistry - 4th edition
Ch. 15.1 - Prob. 15.1PCh. 15.1 - Prob. 15.1PPCh. 15.1 - For trans-2-hexene: (a) draw a stereoisomer; (b)...Ch. 15.2 - Prob. 15.3PCh. 15.2 - Prob. 15.4PCh. 15.3 - Prob. 15.2PPCh. 15.3 - Prob. 15.5PCh. 15.3 - Prob. 15.6PCh. 15.3 - Prob. 15.3PPCh. 15.3 - Prob. 15.7P
Ch. 15.3 - Prob. 15.8PCh. 15.3 - Prob. 15.9PCh. 15.4 - Prob. 15.4PPCh. 15.4 - Prob. 15.10PCh. 15.4 - Prob. 15.11PCh. 15.4 - Prob. 15.12PCh. 15.5 - Prob. 15.13PCh. 15.6 - Prob. 15.5PPCh. 15.6 - Prob. 15.14PCh. 15.6 - Prob. 15.15PCh. 15.7 - Prob. 15.16PCh. 15.7 - Prob. 15.17PCh. 15.7 - Prob. 15.6PPCh. 15.7 - Prob. 15.18PCh. 15.8 - Prob. 15.7PPCh. 15.8 - Prob. 15.19PCh. 15.9 - Prob. 15.20PCh. 15 - Prob. 21PCh. 15 - Prob. 22PCh. 15 - Prob. 23PCh. 15 - Prob. 24PCh. 15 - Prob. 25PCh. 15 - Prob. 26PCh. 15 - Prob. 27PCh. 15 - Prob. 28PCh. 15 - Prob. 29PCh. 15 - Prob. 30PCh. 15 - Prob. 31PCh. 15 - Prob. 32PCh. 15 - Prob. 33PCh. 15 - Prob. 34PCh. 15 - Prob. 35PCh. 15 - Prob. 36PCh. 15 - How are the compounds in each pair related? Are...Ch. 15 - Prob. 38PCh. 15 - Prob. 39PCh. 15 - Prob. 40PCh. 15 - Prob. 41PCh. 15 - Prob. 42PCh. 15 - Prob. 43PCh. 15 - Prob. 44PCh. 15 - Prob. 45PCh. 15 - Prob. 46PCh. 15 - Prob. 47PCh. 15 - Prob. 48PCh. 15 - Prob. 49PCh. 15 - Prob. 50PCh. 15 - (a) Define the terms “optically active” and...Ch. 15 - Prob. 52PCh. 15 - Prob. 53PCh. 15 - Prob. 54PCh. 15 - Prob. 55PCh. 15 - Prob. 56PCh. 15 - Prob. 57PCh. 15 - Prob. 58PCh. 15 - Prob. 59PCh. 15 - Prob. 60PCh. 15 - Prob. 61PCh. 15 - Prob. 62PCh. 15 - Prob. 63PCh. 15 - Prob. 64PCh. 15 - Prob. 65PCh. 15 - Prob. 66PCh. 15 - Prob. 67CPCh. 15 - Prob. 68CP
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- OH ОН Which monosaccharide has a greater heat of combustion, B-D-glucopyranose or B-D-allopyranose? Explain. но НО Но OH OH OH OH OH B-D-Glucopyranose B-D-Allopyranosearrow_forwardClassify each of the following sugars. (For example, glucose is an aldohexose.) CH2OH CH2OH C=0 Но H- HO- C=0 H- H- CH2OH HỌ H- но -H Но ČH;OH ČH2OH CH2OHarrow_forward9 A disaccharide consists of the molecules of D-glucose and D-glucosamine joined by a (1a, 1b)-glucosidic bond. a) Draw the structure of the disaccharide (Haworth projection) if you know that in D- glucose the anomeric carbon has an a-configuration. b) Give the name of the union you drew in question a. c) Draw the structure of the product (cantilever conformation) resulting from the effect of excess acetic anhydride and pyridine on the disaccharide. Hint: D-glucosamine has the same structure as D-glucose, but C-2 has an amino group instead of a hydroxyl.arrow_forward
- Classify the structures as being either an enantiomer, diastereomer or diastereomer/epimer of D-glucose. Structure A: CH H- -OH Structure B: но- H- H- OH Structure C: H- он H- -H D-Glucose: OH || CH CH CH он H- он но -H H- он но он но но- H- но H- OH OH но -- H- -H H -Ç-H Structure A: OH Structure B: OH Structure C: OHarrow_forwardm) 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_forwardA Fischer projection of a monosaccharide is shown below: CH₂OH C=O H НО HO -OH H H CH₂OH a. Classify this monosaccharide (e.g., aldotriose) b. Does it have the D or L configuration? c. Which carbon and oxygen become bonded in the furanose ring form of this monosaccharide (e.g., C206, where 06 means the oxygen on carbon 6, or "not formed")? d. Which carbon and oxygen become bonded in the pyranose ring form of this monosaccharide e.g., C206 or "not formed"?arrow_forward
- 5. Consider the following pairs of structures. Identify the relationship between them (enantiomers, diastereomers, or identical compounds. он HO o CH,OH H,C H но CH,OH сон H HO. HO CH, HO,C CH COH HO,C, CO,H CO,H н онн он н онн он HOH,C сно OHC CH,OH Br CH,CH, H,CH,C CI CH OHarrow_forward5. Cholesterol is one of the important component of animal cell membrane. Label circled chiral centers as R/S, and circle the rest of chiral centers in this compound. b a H НО Cholesterolarrow_forwardDraw the isomers for each aldotetrose and ketopentose in the figure below and designate each isomer as a D or L sugar and designate also the R and S in every chiral centers. Label the enantiomers and diastereomers respectively. CH,OH C=0 Н—С—ОН Н-С—ОН Н—С—ОН H-C-OH ČH,OH ČH,OHarrow_forward
- Two sugars differing in configuration at a single asymmetric carbon atom are known as epimers. D-mannose is a C-2 epimer of glucose (Structure I), while D-galactose is a C-4 epimer of glucose. Structure Il and IIl are H- -OH но- -H H OH HO H но- H HO H H -OH H- -OH HO OH H -OH H- -OH H OH HO. HO, OH II II Which of the following represents an aldopentose? OH H O HO O HO H но н HO H но- HO H HO H HO- H OH H OH H OH H OH OH HO Он of но" HO O OH он III IV These are chemical messengers that are secreted by endocrine glands and carried through the bloodstream to target tissues. prostaglandin deoxysugar glycoside hormones Which of the following is NOT correctly paired? cellulose: beta-1,4-glycosidic linkage amylose: alpha-1,4-glycosidic linkage chitosan: alpha-1,4-glycosidic linkage cellubiose: beta-1,4-glycosidic linkagearrow_forwardThe structure of 4 isomers of ketopentose are shown. 1) select every structure that is a diastereomer of structure D A, B, or C? 2) select every structure that is a enantiomer of structure C A, B, or D 3) select every structure that is a stereoisomer of structure C A, B, or Darrow_forwardTomnaLS Page < 3 7. For each disaccharide, indicate whether the glycosidic linkage is a or ß. CH,OH CH,OH OH но OH OH ОН ОН CH2OH OH но OH CH 2 HO O OH OH OH Identify each Fischer projection as the D- or L-isomer.arrow_forward
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