EBK ORGANIC CHEMISTRY
8th Edition
ISBN: 8220102744127
Author: Bruice
Publisher: PEARSON
expand_more
expand_more
format_list_bulleted
Concept explainers
Question
Chapter 4, Problem 101P
Interpretation Introduction
Interpretation:
The assigning of configuration of each asymmetric center as R if –OH group is on the right and the configuration is S if the –OH is group in on left side for D-glucose has to be checked.
Concept introduction:
- Asymmetric center is a stereocenter which arises to a compound if any atom is bonded to four different groups.
- The stereo-descriptor for other carbohydrates of having more than one chiral center will be evaluated by the location of –OH group (right or left) of farthest chiral carbon from the carbonyl group. Such as,
If the –OH group is located in right side then, the carbohydrate is a D-sugar.
If the –OH group is located in left side then, the carbohydrate is a L-sugar.
- Configuration of a molecule: The configurations of a molecule arise due to the spatial arrangement of atoms. The configuration can be assigned by following CIP rules as follows.
- Assign numbering to the groups which are bonded to the chiral carbon based on the molecular weight and electronegativity.
- If the sequence of the numbering follows clockwise direction the chiral atom is assigned as R configuration.
- If the sequence of the numbering follows anticlockwise direction the chiral atom is assigned as S configuration.
- If the least priority group is on horizontal line in the fisher projection, then configuration is inverted to the obtained configuration from the above CIP rule which means R configuration becomes S and vice versa.
Expert Solution & Answer
Trending nowThis is a popular solution!
Students have asked these similar questions
1) Below you are given the structures of the disaccharides lactose and trehalose.
он
он
но
он
но
но
OH
но
но
OH
но
он
но
но
OH
Lactose
Trehalose
a. Identify clearly the hemiacetal and acetal groups in these disaccharides and determine for each
of these identified groups if they have a- or B-configuration.
A student decided that the configuration of the asymmetric centers in a sugar such as d-glucose could be determined rapidly by simply assigning the R configuration to an asymmetric center with an OH group on the right and the S configuration to an asymmetric center with an OH group on the left. Is he correct?
Draw the structure of the disaccharide maltose (-D-glucopyranosyl (1→4)-D-glucopyranose). Indicate with arrows the reducing end and the acetal functional group.
Chapter 4 Solutions
EBK ORGANIC CHEMISTRY
Ch. 4.1 - Prob. 2PCh. 4.1 - Prob. 3PCh. 4.1 - Prob. 4PCh. 4.1 - Prob. 5PCh. 4.1 - Which of the roll owing compounds have a dipole...Ch. 4.2 - Draw and label the E and Z isomers for each of the...Ch. 4.2 - Assign relative priorities to each set of...Ch. 4.2 - Tamoxifen slows the growth of some breast tumors...Ch. 4.2 - Prob. 10PCh. 4.2 - Name each of the following:
Ch. 4.2 - Draw the Z isomer of an alkene that has a CH3 and...Ch. 4.3 - Prob. 13PCh. 4.4 - Prob. 14PCh. 4.5 - Prob. 16PCh. 4.6 - Prob. 17PCh. 4.7 - Prob. 18PCh. 4.8 - Prob. 20PCh. 4.8 - Prob. 22PCh. 4.8 - Prob. 23PCh. 4.8 - Prob. 24PCh. 4.8 - Draw a perspective formula for each or the...Ch. 4.8 - Prob. 27PCh. 4.9 - Prob. 28PCh. 4.9 - What is the configuration of the following...Ch. 4.9 - Prob. 32PCh. 4.10 - Prob. 33PCh. 4.10 - (S)-(+)-Monosodium glutamate (MSG) is a flavor...Ch. 4.11 - Prob. 35PCh. 4.11 - Prob. 36PCh. 4.12 - Prob. 38PCh. 4.12 - Prob. 39PCh. 4.12 - The stereoisomer of cholesterol found in nature is...Ch. 4.12 - Prob. 41PCh. 4.13 - 1-Bromo-2-methylcyclopentane has four pairs of...Ch. 4.13 - Prob. 43PCh. 4.13 - Draw all possible stereoisomers for each of the...Ch. 4.13 - Prob. 45PCh. 4.13 - Of all the possible cyclooctanes that have one...Ch. 4.13 - Prob. 47PCh. 4.13 - Prob. 48PCh. 4.14 - Which of the following compounds has a...Ch. 4.14 - Draw all the stereoisomers for each of the...Ch. 4.15 - Prob. 52PCh. 4.15 - Name the isomers you drew in Problem 52.Ch. 4.15 - Chloramphenicol is a broad-spectrum antibiotic...Ch. 4.15 - Draw a perspective formula for each of the...Ch. 4.15 - Name the following:Ch. 4.15 - Prob. 57PCh. 4.15 - Prob. 59PCh. 4.15 - Convert the perspective formula to a skeletal...Ch. 4.15 - Prob. 62PCh. 4.16 - Prob. 63PCh. 4.17 - Limonene exists as two different stereoisomers....Ch. 4 - a. Draw three constitutional isomers with...Ch. 4 - Prob. 65PCh. 4 - Prob. 66PCh. 4 - Which of the following has an asymmetric center?...Ch. 4 - Prob. 68PCh. 4 - Prob. 69PCh. 4 - Prob. 70PCh. 4 - Prob. 71PCh. 4 - Assign relative priorities to each set of...Ch. 4 - Prob. 73PCh. 4 - Which of the following are optically active?Ch. 4 - Prob. 75PCh. 4 - Name the following:Ch. 4 - Which of the following has an achiral...Ch. 4 - Using skeletal structures, draw the stereoisomers...Ch. 4 - Prob. 79PCh. 4 - Citrate synthase, one of the enzymes in the series...Ch. 4 - Prob. 81PCh. 4 - Prob. 82PCh. 4 - Prob. 83PCh. 4 - Prob. 84PCh. 4 - Prob. 85PCh. 4 - Prob. 86PCh. 4 - Prob. 87PCh. 4 - Prob. 88PCh. 4 - Prob. 89PCh. 4 - a. Draw all the isomers with molecular formula...Ch. 4 - Prob. 91PCh. 4 - Prob. 92PCh. 4 - Draw structures for the following: a....Ch. 4 - For each of the following structures, draw the...Ch. 4 - Prob. 95PCh. 4 - Prob. 96PCh. 4 - Prob. 97PCh. 4 - a. Using the wedge-and-dash notation, draw the...Ch. 4 - Prob. 99PCh. 4 - Prob. 100PCh. 4 - Prob. 101PCh. 4 - a. Draw the two chair conformers for each of the...Ch. 4 - Prob. 103PCh. 4 - Is the following compound optically active?Ch. 4 - Prob. 105P
Knowledge Booster
Learn more about
Need a deep-dive on the concept behind this application? Look no further. Learn more about this topic, chemistry and related others by exploring similar questions and additional content below.Similar questions
- 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_forwardGlycosaminoglycans (GAGs) are heteropolysaccharides composed of repeating disaccharide units. These units have some similar characteristics that allow them to be identified as GAGS. Which of the structures are examples of glycosaminoglycans? А. C. E. HO HO COO™ H Н ОН Н CH₂OH H H H OH OH Н CH₂OH Н OH H ОН o,so H H Н CH₂OH H H ОН H CH₂OSO H NH C=0 CH, H H Н NH c=0 CH3 H CH,OH OH Н ОН OH H B. D. Н НО H ОН H CH₂OH H ОН Н СОО ОН Н Н H H OSoz H Н OH б H CH₂OH ОН CH₂OSO H ОН H Н OSO, H Н NHSO,arrow_forwardH8. Determine which one of these are diastereomers, enantiomers, identical, or other (none of the above).arrow_forward
- The disaccharide lactose is built up by one D-galacto- and one D-gluco monosaccharide unit. Draw L-galactose in the Fischer projection (open) form and in its most stable pyranose ring conformation form and determine if the latter is a 1C4 or a 4C1 conformation.arrow_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_forwardComplete the following for each of the following structures below. Determine whether it is an aldohexose, aldopentose, ketohexose or ketopentose. Label the chiral carbon atoms using an asterisk. Determine the number of stereoisomers it can have. Label the molecule as a D or an L sugar.arrow_forward
- Identify all carbon chiral centers in cocaine.arrow_forwardTwo 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 II and III are II: galactose, III: mannose II: mannose; III: galactose II and III are mannose II and III are galactosearrow_forwardIdentify the chiral centers in the following molecule and label each as r and s.arrow_forward
- Q1: What structural relationship is indicated by the term D-sugar? Why are (+) glucose and (−) fructose both classified as D-sugars? Write the principal functional roles of D-glucose, D-fructose and galactosearrow_forward-Sketch the Fischer projection and make a model of each stereoisomer (R and S) of the alcohol 2-butanol, CH3CHOHCH2CH3. Also sketch the monosaccharide glyceraldehyde, HOCH2CHOHCHO. Prioritize the four groups attached to the stereocenter with 1 being the highest priority and 4 being the lowest priority.arrow_forwardThe structure of an enzyme inhibitor is given. Identify the chirality center(s) in the structure. N NH F\ 0= Identify the chirality center(s).arrow_forward
arrow_back_ios
SEE MORE QUESTIONS
arrow_forward_ios
Recommended textbooks for you
- Introduction to General, Organic and BiochemistryChemistryISBN:9781285869759Author:Frederick A. Bettelheim, William H. Brown, Mary K. Campbell, Shawn O. Farrell, Omar TorresPublisher:Cengage LearningChemistry for Today: General, Organic, and Bioche...ChemistryISBN:9781305960060Author:Spencer L. Seager, Michael R. Slabaugh, Maren S. HansenPublisher:Cengage LearningGeneral, Organic, and Biological ChemistryChemistryISBN:9781285853918Author:H. Stephen StokerPublisher:Cengage Learning
- Organic And Biological ChemistryChemistryISBN:9781305081079Author:STOKER, H. Stephen (howard Stephen)Publisher:Cengage Learning,Organic Chemistry: A Guided InquiryChemistryISBN:9780618974122Author:Andrei StraumanisPublisher:Cengage Learning
Introduction to General, Organic and Biochemistry
Chemistry
ISBN:9781285869759
Author:Frederick A. Bettelheim, William H. Brown, Mary K. Campbell, Shawn O. Farrell, Omar Torres
Publisher:Cengage Learning
Chemistry for Today: General, Organic, and Bioche...
Chemistry
ISBN:9781305960060
Author:Spencer L. Seager, Michael R. Slabaugh, Maren S. Hansen
Publisher:Cengage Learning
General, Organic, and Biological Chemistry
Chemistry
ISBN:9781285853918
Author:H. Stephen Stoker
Publisher:Cengage Learning
Organic And Biological Chemistry
Chemistry
ISBN:9781305081079
Author:STOKER, H. Stephen (howard Stephen)
Publisher:Cengage Learning,
Organic Chemistry: A Guided Inquiry
Chemistry
ISBN:9780618974122
Author:Andrei Straumanis
Publisher:Cengage Learning