a)
Interpretation:
The ranking of the substituent is to done from the following sets of substituent.
Concept introduction:
Rule 1:
a) Higher
b) An atom node duplicated closer to the root ranks higher than one duplicated further.
Rule 2: Higher
Rule 3: Z precedes E and this precedes nonstereogenic (nst) double bonds.
Rule 4:
a) Chiral stereogenic units precede pseudoasymmetric stereogenic units and these precede nonstereogenic units (R = S > r = s > nst).
b) When two ligards have different descriptor pairs, the one with the first chosen like descriptor pairs has priority over the one with a corresponding unlike descriptor pairs.
c) r precedes s.
Rule 5: An atom or group with descriptor R has priority over its enantiomorph S.
b)
Interpretation:
The ranking of the substituent is to done from the following sets of substituent.
Concept introduction:
Rule 1:
a) Higher atomic number precedes lower.
b) An atom node duplicated closer to the root ranks higher than one duplicated further.
Rule 2: Higher atomic mass number precedes lower.
Rule 3: Z precedes E and this precedes nonstereogenic (nst) double bonds.
Rule 4:
a) Chiral stereogenic units precede pseudoasymmetric stereogenic units and these precede nonstereogenic units (R = S > r = s > nst).
b) When two ligards have different descriptor pairs, the one with the first chosen like descriptor pairs has priority over the one with a corresponding unlike descriptor pairs.
c) r precedes s.
Rule 5: An atom or group with descriptor R has priority over its enantiomorph S.
c)
Interpretation:
The ranking of the substituent is to done from the following sets of substituent.
Concept introduction:
Rule 1:
a) Higher atomic number precedes lower.
b) An atom node duplicated closer to the root ranks higher than one duplicated further.
Rule 2: Higher atomic mass number precedes lower.
Rule 3: Z precedes E and this precedes nonstereogenic (nst) double bonds.
Rule 4:
a) Chiral stereogenic units precede pseudoasymmetric stereogenic units and these precede nonstereogenic units (R = S > r = s > nst).
b) When two ligards have different descriptor pairs, the one with the first chosen like descriptor pairs has priority over the one with a corresponding unlike descriptor pairs.
c) r precedes s.
Rule 5: An atom or group with descriptor R has priority over its enantiomorph S.
d)
Interpretation:
The ranking of the substituent is to done from the following sets of substituent.
Concept introduction:
Rule 1:
a) Higher atomic number precedes lower.
b) An atom node duplicated closer to the root ranks higher than one duplicated further.
Rule 2: Higher atomic mass number precedes lower.
Rule 3: Z precedes E and this precedes nonstereogenic (nst) double bonds.
Rule 4:
a) Chiral stereogenic units precede pseudoasymmetric stereogenic units and these precede nonstereogenic units (R = S > r = s > nst).
b) When two ligards have different descriptor pairs, the one with the first chosen like descriptor pairs has priority over the one with a corresponding unlike descriptor pairs.
c) r precedes s.
Rule 5: An atom or group with descriptor R has priority over its enantiomorph S.
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Chapter 5 Solutions
Organic Chemistry
- 17-54 Following is the structure of immunosuppressant FK-506, a molecule shown to disrupt calcineurin-mediated signal transduction in T-lymphocytes. (a) There are three carbon—carbon double bonds present in this molecule. Which of the three has the potential for cis/trans isomerism? Assign a cis or trans con?guration to each carbon-carbon double bond that has this possibility. (b) How many stereocenters are present in this molecule? How many stereoisomers are possible for it? (c) Are there any aromatic components in this molecule? (d) Consider the two carbon atoms marked with asterisks. Assign an R or S con?guration of each stereocenter. (e) Because of the presence of a 21-member ring, this molecule is described as a macrocycle. This ring is fashioned by three types of bonds, several carbon-carbon bonds, one ester, one hemiacetal, and one amide. Locate the ester and the hemiacetal. (f) Draw the structural formula of the long chain compound that would result if the hemiacetal were to be cleaved to an alcohol and a carbonyl group.arrow_forward5-54 Ribose, an essential part of ribonucleic acid (RNA), has the following structure: H H H OH CHO Ribose Но но н но н (a) How many chirality centers does ribose have? Identify them. (b) How many stereoisomers of ribose are there? (c) Draw the structure of the enantiomer of ribose. (d) Draw the structure of a diastereomer of ribose.arrow_forwardA compound that contains two different stereocenters can exist as four optically active stereoisomers. The flying wedge representations of the four stereoisomers are given below: ÇOOH ÇOOH ÇOOH ÇOOH H-C-OH HO-C-H H-C-OH HO-C-H H-C-OH HO-C-H HO-C-H H-C-OH ČH3 ČH3 ČH3 ČH3 II II IV What is the relationship between: 96.I and II? 97. I and IV? 98. I and III? II and III? III and IV? II and IV?arrow_forward
- 15-31 (Che drug synt. the c 15-25 Label all stereocenters in each molecule with an asterisk. How many stereoisomers are possible for each molecule? are OH form sin c (a) (b) usec OH chir each Сap ture (c) он (d)arrow_forwardClassify the following pair of compounds as the same compound, enantiomers, diastereomers, constitutional isomers, or not isomeric. Also, select the correct IUPAC name, including the correct (R) or (S) designation, for each. H ÷ ||I The correct IUPAC names are: || J k CI same compound enantiomers diastereomers constitutional isomers not isomeric Compound I: (2R, 3R)-2,3-dichloropentane, Compound II: (2R, 3S)-2,3-dichloropentane Compound I: (2S, 3S)-2,3-dichloropentane, Compound II: (2S, 3S)-2,3-dichloropentane Compound I: (2S, 3R)-2,3-dichloropentane, Compound II: (2S, 3R)-2,3-dichloropentane Compound I: (2R, 3R)-2,3-dichloropentane, Compound II: (2R, 3R)-2,3-dichloropentanearrow_forward18 Mark each stereocenter in these molecules with an asterisk. Note that not all contain stereocenters. (a) OH CH, N. `CH3 (b) OH (c) HO, NH2 (d)arrow_forward
- What is true about the relationship between the following compounds? CH3 CH3 CH; CH; CH3 CH3 A В O All three are stereoisomers of each other. OA and B are the same compound while C is a stereoisomer. All three are the same compound. A and B are the same while C is a conformer, all of the same compound . O A and C are the same while B is a stereoisomer.arrow_forward5-65 Draw tetrahedral representations of the following molecules: (a) The 2S,3R enantiomer of 2,3-dibromopentane (b) The meso form of 3,5-heptanediolarrow_forwardH₂SO4 140°C 2CH₂CH₂CH₂CH₂-OH- H₂O +arrow_forward
- 15-43 Triamcinolone acetonide, the active ingredient in Azmacort Inhalation Aerosol, is a steroid used to treat bronchial asthma. Triamcinolone acetonide Label the eight stereocenters in this molecule. How many stereoisomers are possible for it? (Of these, the stereoisomer with the configura tion shown here is the active ingredient in Azmacort.)arrow_forward• Consider the following compounds. Assign the R or S configuration to each stereogenic center (add answers onto structures): CH,CH, OCH3 CH3 CH,CH3 сно H;CO,C NH2 co,H 18 Assign the absolute configuration at the stereogenic centre C3 of compound Y. OH Compound Y Assign the absolute configuration at the stereogenic centre C2 of compound Y. Br HO 1 CF3 bund Y Assign the absolute configuration at the stereogenic centre(s) C2 abd C3 of compound Y. HO, HO, 20 Compound Y רarrow_forwardFollowing are stereorepresentations for the four stereoisomers of 3-chloro-2-butanol. (a) Assign an R or S configuration to each chiral center. (b) Which compounds are enantiomers? (c) Which compound are diastereomers?arrow_forward
- Introduction to General, Organic and BiochemistryChemistryISBN:9781285869759Author:Frederick A. Bettelheim, William H. Brown, Mary K. Campbell, Shawn O. Farrell, Omar TorresPublisher:Cengage Learning