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 CHEM. VOL.1+2-W/WILEYPLUS
- What is the maximum number of stereoisomers possible for a compound with: (a) three stereogenic centers; (b) eight stereogenic centers?arrow_forward) How many chiral centers are present in desosamine? How many stereoisomers are possible for it? How many pairs of enantiomers are possible for it?arrow_forwardKk.40.arrow_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_forwardA is a toxin produced by the poisonous seaweed Chlorodesmis fastigiata. (a) Label each alkene that exhibits stereoisomerism as E or Z. (b) Draw a stereoisomer of A that has all Z double bonds.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
- 4.31 Diltiazem is prescribed to treat hypertension, and simvastatin is a cholesterol-lowering drug. Locate the chirality centers in each. (CH3)2N НО, N- || -ОССH, H;C CH3 CH3 ОСНЗ H3C Diltiazem Simvastatinarrow_forward3. Cinnamic acid (shown) reacts with bromine to give a bromination product. (a) Draw all four possible stereoisomers of this reaction as a Fischer projection. Label each molecule as A, B, C, and D. (b) Identify the pairs of enantiomers (c) Identify the pairs of diastereomers (d) Identify which pair corresponds to addition to trans-cinnamic acid. Briefly explain your reasoning. O OH Br₂ CH₂Cl₂arrow_forward3.3 Draw line structures of (a) an enantiomer and (b) a diastereomer of Compound L. OH NH2 Compound Larrow_forward
- 4.28 In each of the following pairs of compounds one is chiral and the other is achiral. Identify each compound as chiral or achiral, as appropriate. ОН НО ОН (a) and ОН Cl Br (b) Br and CH3 CH3 -NH2 H2N (c) H and H -NH2 H NH2 CH3 CH3 (d) and ОН (e) ОН and ОН ОН H3C (f) CH3 and ОН ОН (g) andarrow_forwardNonearrow_forward1. Which of the following molecules are chiral? Identify the chirality center(s) in each. (a) -CH3 (b) -CH2CH2CH3 (c) CH3CH2 Toluene Coniine (from poison hemlock) H. Phenobarbital (tranquilizer) 2. A 1.50 g sample of coniine, the toxic extract of poison hemlock, was dissolved in 10.0 mL of ethanol and placed in a sample cell with a 5.00 cm pathlength. The observed rotation at the sodium D line was +1.21°. Calculate [a]p for coniine. 3. Rank the substituents in each of the following sets: (а) -Н, -ОН, -CH-CH3, -СH>СH,ОН (b) -СО-Н, -СО,CH3, -СH2ОH, -он (c) -CN, -CH2NH2, -CH2NHCH3, –NH2 (d) –SH, –CH2SCH3, –CH3, –SSCH3 4. Assign R,S configurations to the following molecules: (a) Br (b) H (c) NH2 H3C-CO2H HOC-CO2H CH3 NCC-CH3 H H 5. Assign R or S configuration to each chirality center in the following molecules: (a) Br (b) CH3 CH3 HaBr (c) HaCH3 BraH H3C" OH H CH3 OH CH3 OH Which of these compounds are enantiomers, and which are diastereomers? 6. Which of the following substances have meso…arrow_forward
- Organic ChemistryChemistryISBN:9781305580350Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. FootePublisher:Cengage Learning