Concept explainers
Interpretation:
In compounds A and B, the
Concept Introduction:
The molecules which are non-superimposable or not identical with its mirror image are known as chiral molecules.
The pair of two mirror images which are non-identical are known as enantiomers and these are optically active.
The enantiomers, in which the path traced from the highest
The enantiomers, in which the path traced from the highest atomic number to the lowest atomic number is in the clockwise direction, are designated as
The objects or molecules which are superimposable with its mirror images are achiral objects or molecules and these objects have a centre of symmetry or plane of symmetry.
The achiral compounds in which the plane of symmetry is present internally and consists of chiral centres are known as meso compounds, but they are optically inactive.
The stereoformula which is depicted in two dimensions, in which stereochemical information is not destroyed, is determined by the Fisher Projection formula.
The stereoisomers which are non-superimposable on each other and not mirror images of each other are known as diastereomers.
Chiral molecules are capable of rotating plane polarized light
The molecules which are superimposable or identical with their mirror images are known as achiral molecules, and achiral molecules are not capable of rotating the plane-polarised light.
Plane of symmetry is the plane that bisects the molecule in two equal halves, such that they are mirror images of each other.
Compounds having plane of symmetry are usually achiral as they do not have different atoms around the central carbon atom.
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Organic Chemistry
- If molecules A and B are isomers of each other, then what kinds of isomers could they be (i.e., enantiomers, diastereomers, or constitutional isomers) under each of the following conditions?(a) Both molecules have the same IHD.(b) Molecule A has a ring but molecule B does not.(c) Molecules A and B contain different functional groups.(d) Molecules A and B share exactly the same functional groups.(e) Molecule A has a plane of symmetry but molecule B does not.arrow_forward(A) How many chirality centers does the following molecule contain? (B) How many stereoisomers are possible for this molecule? (C) Assign R,S designation to each chiral carbonarrow_forward5.75 An acid-base reaction of (R)-sec-butylamine with a racemic mixture of 2- phenylpropanoic acid forms two products having different melting points and somewhat different solubilities. Draw the structure of these two products. Assign R and S to any stereogenic centers in the products, How are the two products related? Choose from enantiomers, diastereomers, constitutional isomers, or not isomers of each other. OH NH2 2-phenyipropanoic acid (racemic mixture) Rsec-butylaminearrow_forward
- Draw the structure for a compound with molecular formula C2H2I2F2 a. that is optically inactive because it does not have an asymmetric center. b. that is optically inactive because it is a meso compound. c. that is optically active.arrow_forward(a) Locate the stereogenic centers in the ball-and-stick model of ezetimibe (trade name Zetia), a cholesterol-lowering drug. (b) Label each stereogenic center as R or S. ezetimibearrow_forwardEleostearic acid is an unsaturated fatty acid obtained from the seeds of the tung oii tree (Aleurites fordii), a deciduous tree native to China. (a) Draw the structure of a stereoisomer that has a higher melting point than eleostearic acid. (b) Draw the structure of a stereoisomer that has a lower melting point. CO,H eleostearic acidarrow_forward
- (a) assign R or S configuration to each chiral center, (b) Which compound are enantiomers? (c) Which compounds are diastereomers?arrow_forwardConsider (2R,3R)-2,3-diidobutane: (a) Draw a Fischer Projection of this structure with Cı on top and C4 on bottom. (b) Draw a Newman Projection of of the meso compound of 2,3-dibromobutane looking down the C2-C3 bond with C2 in front, and label your asymmetric carbons as S or R.arrow_forward5.73 Identify the specific relationship between each of the following pairs of molecules (i.e., either same, constitutional isomers, enantiomers, diastereomers, conformers, or unrelated). (a) H CH, (d) (g) НО НО H HO H H -CI CI CH3 H a CH₂ CO H OH H OH CH₂OH CI- OH CH₂ H H НО Н НО OH CH₂ (b) OH H CO H HO (0) H H H CH OH (h) H CH₂ CI CI- CO.H H CH₂OH НО H -OH HO OH НО OH HO CO H OH H OH CO₂H H OH CO.H H НО -H CH OH H H НО CO H -H (c) (1) OH H CO H НО H- Н- H Н -CI H₂C- CH₂ со н OH Н OH HO OH Н CH₂OH OH CI со н -H OH -Н OH CH.OHarrow_forward
- 5.40 Consider the following pairs of structures. Designate cach chirality center as (R) or (S) and identify the relationship bêtween them by describing them as representing enantiomers, diastereomers, constitutional isomers, or two molecules of the same compound. Use handheld molecular models to check your answers. Br CH, H,C Br (a) () and and ĆI CI H. CH H,C H CH3 CH3 (b) and F Br Br F CI CI -H- (k) H- and CH, Br CH, Br H. -CI H- CI (c) H,CH and F CH3 CH3 CH3 Br H,C H. Br H- (1) -CI Br- CH3 and HH CI- Br (d) F CH, H and Fu CH3 Hi Br CH, H,C CH3 F H Br (m) and (e) H,C and "F HC H Br H. CH Br and (n) and CH3 CI (0) and CH3 Br H,CC. Br and Ci Ci CI CI (h) Cl- and -CI (p) and ČI ČI CI Ci CI Br and (q) Br Br C=C=CH C=Cc=CBr and ČI CI HICarrow_forward• PRACTICE PROBLEM 5.22 Write three-dimensional formulas for all of the stereoisomers of each of the following compounds. Label pairs of enantiomers and label meso compounds. enslg a nsudomotaib esvierd ofni oluelom oreovb dase to ope.n 1oim s ier 1erto (a) ibaong (b) A boemo OH (c) CI ОН CI F F OH win vle (f) HO,C. (d) (e) OH CI CO,H Br im slm (b) OH Tartaric acidarrow_forward5.69 Carvone is present in many essential oils. It is chiral, and its two enantiomers are shown here. Even though they are enantiomers, they have different odors. The (-) enantiomer smells like spearmint, whereas the (+) enantiomer smells like caraway seeds. What does this say about the olfactory receptors that detect carvone? than a plana) HROO HO HO HO H00 osses O= Datum his H. HO HO HO Tefur OH Hie ane 2000 (-)-Carvone OH muistad Y (+)-Carvone HO yet it pelesses no Harrow_forward
- Organic ChemistryChemistryISBN:9781305580350Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. FootePublisher:Cengage Learning