Organic Chemistry (8th Edition)
8th Edition
ISBN: 9780134042282
Author: Paula Yurkanis Bruice
Publisher: PEARSON
expand_more
expand_more
format_list_bulleted
Concept explainers
Question
Chapter 4.15, Problem 57P
Interpretation Introduction
Interpretation:
The structure that represents the naturally occurring amino acid has to be identified.
Concept introduction:
The configuration of stereoisomer is determined by Cahn-Ingold-Prelog system rules.
According to Cahn-Ingold-Prelog system,
The group attached to asymmetric center should be ranked based on the
Check the direction of arrow drawn in the direction of decreasing priority. If the arrow points clockwise direction, then the compound has R configuration. If the arrow points counterclockwise direction, then the compound has S configuration. If the group with lowest priority is not bonded by a hatched wedge, then interchange this group (lowest priority) by group bonded to hatched wedge and draw the arrow in priority order but the configuration is assigned as just reverse.
Expert Solution & Answer
Want to see the full answer?
Check out a sample textbook solution
Students have asked these similar questions
Threonine, an amino acid, has four stereoisomers. The stereoisomer found in nature is (2S,3R)-threonine. Which of the following structures represents the naturally occurring amino acid?
(a) Describe the molecular geometry expected for 1,2,3-butatriene (H2C=C=C=CH2). (b) Two stereoisomers are expected for 2,3,4-hexatriene (CH3CH=C=C=CHCH3). What should be the relationship between these two stereoisomers?
Q2 Give the stereochemical relationships between each pair of structures. Examples are
same compound, structural isomers, enantiomers, diastereomers
fa
CH.
OH HO-
OR HO
CH,
CH.
CH,
Chapter 4 Solutions
Organic Chemistry (8th Edition)
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
- For each of the following compounds,determine whether each is optically active. For optically active compounds, identify the chiral carbon: ethane, 2-chloro-2-methylbutane, CH3CH(NH2)COOH, CH3CH2CHClCH3and CH3CH2CH2CH3. And for non-optical active compounds, just provide the structure of the compoundarrow_forwardMaleic acid and fumaric acid are the cis- and trans- isomers, respectively, of C2H2(COOH)2, a dicarboxylic acid. Draw and label their structures.arrow_forwarda) If the pH value of an aqueous solution of trimethylamine [(CH3) 3N] is 10.75, what should be the molarity of this solution? (CH3) 3N + H2O ↔ (CH3) 3NH + + OH-, Kb = 6.3 × 10-5 b) What will be the pH of the solution prepared by dissolving 8.35 g of aniline hydrochloride (C6H5NH3 + Cl-) in 750 mL of 0.215 M aniline (C6H5NH2)? Is this solution an effective buffer? Explain (Kb = 7.4 × 10-10 for aniline, C: 12.0 g / mol, H: 1.0 g / mol, N: 14.0 g / mol, Cl: 35.4 g / mol) .arrow_forward
- What is the degree of unsaturation for C6H8? Draw two possible structures.arrow_forwarda) If the pH value of an aqueous solution of trimethylamine [(CH3)3N] is 10.75, what should be the molarity of this solution? (CH3)3N + H2O ↔ (CH3)3NH+ + OH-, Kb = 6,3 × 10-5 b) What will be the pH of the solution prepared by dissolving 8.35 g of aniline hydrochloride (C6H5NH3+Cl-) in 750 mL of 0.215 M aniline (C6H5NH2)? Is this solution an effective buffer? Explain (Kb = 7,4 × 10-10 for aniline, C: 12.0 g / mol, H: 1.0 g / mol, N: 14.0 g / mol, Cl: 35.4 g / mol) .arrow_forwardA well known non steroidal anti inflammation drug NSAID exists in two sterochemical forms. Only one is biologically active. Below is the structure of the biological active form. Identify the chiral center and determine if it is the R- or S- stereoisomer.arrow_forward
- Which statements are true about constitutional isomers? (a) They have the same molecular formula. (b) They have the same molecular weight. (c) They have the same order of attachment of atoms. (d) They have the same physical propertiesarrow_forward(a) Draw the nine isomers having the formula C7H16 . (Hint: There is one structure with a seven-carbon chain, two structures with six-carbon chains [one is illustrated in the margin above], five structures with a five-carbon chain, and one structure with a fourcarbon chain.)(b) Identify the isomers of C7H16 that are chiral.arrow_forwardThe [α] of pure quinine, an antimalarial drug, is −165.Calculate the ee of a solution with the following [α] values: −50, −83,and −120.For each ee, calculate the percent of each enantiomer present.What is [α] for the enantiomer of quinine?If a solution contains 80% quinine and 20% of its enantiomer, what isthe ee of the solution?What is [α] for the solution described in part (d)?arrow_forward
- Most naturally occurring amino acids have chiral centers (the asymmetric a carbon atoms)that are named (S) by the Cahn–Ingold–Prelog convention (Section 5-3). The commonnaturally occurring form of cysteine has a chiral center that is named (R), however.(a) What is the relationship between (R)-cysteine and (S)-alanine? Do they have the oppositethree-dimensional configuration (as the names might suggest) or the same configuration?(b) (S)-Alanine is an l-amino acid (Figure 24-2). Is (R)-cysteine a d-amino acid or anl-amino acid?arrow_forwardThe quantitative differences in biological activity between the two enantiomers of a compound are sometimes quite large. For example, the D isomer of the drug isoproterenol, used to treat mild asthma, is 50 to 80times more effective as a bronchodilator than the L isomer. Identify the chiral center in isoproterenol. Why do the two enantiomers have such radically different bioactivity?arrow_forwardDraw all possible constitutional isomers and stereoisomers of C4H8. There should be 6 structures.arrow_forward
arrow_back_ios
SEE MORE QUESTIONS
arrow_forward_ios
Recommended textbooks for you
Chemistry: Principles and ReactionsChemistryISBN:9781305079373Author:William L. Masterton, Cecile N. HurleyPublisher:Cengage Learning
Chemistry: The Molecular ScienceChemistryISBN:9781285199047Author:John W. Moore, Conrad L. StanitskiPublisher:Cengage Learning
Chemistry: Matter and ChangeChemistryISBN:9780078746376Author:Dinah Zike, Laurel Dingrando, Nicholas Hainen, Cheryl WistromPublisher:Glencoe/McGraw-Hill School Pub Co
Organic ChemistryChemistryISBN:9781305580350Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. FootePublisher:Cengage Learning
Chemistry: Principles and Reactions
Chemistry
ISBN:9781305079373
Author:William L. Masterton, Cecile N. Hurley
Publisher:Cengage Learning
Chemistry: The Molecular Science
Chemistry
ISBN:9781285199047
Author:John W. Moore, Conrad L. Stanitski
Publisher:Cengage Learning
Chemistry: Matter and Change
Chemistry
ISBN:9780078746376
Author:Dinah Zike, Laurel Dingrando, Nicholas Hainen, Cheryl Wistrom
Publisher:Glencoe/McGraw-Hill School Pub Co
Organic Chemistry
Chemistry
ISBN:9781305580350
Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Publisher:Cengage Learning