Concept explainers
Interpretation:
The configuration
Concept Introduction:
▸ The molecules which are non-superimposable or not identical with their mirror images are known as chiral molecules.
▸ A pair of two mirror images which are non-identical is known as enantiomers which are optically active.
▸ The objects or molecules which are superimposable with their mirror images are achiral objects or molecules and these objects have a centre of symmetry or plane of symmetry.
▸ The achiral compounds in which plane of symmetry is present internally and consists of chiral centres are known as meso compounds but they are optically inactive.
▸ 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.
▸ Priority is given to all the four group attached to the chirality center.
▸ Priority is assigned according to the
▸ If priority cannot be assigned according to
▸ After giving priority to the four groups, rotate the molecule such that the fourth priority group is away from the observer.
▸ Now, move from a to b to c; if the direction is clockwise, then the chiral center is designated as
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Organic Chemistry
- 5:51 Draw examples of the following: (a) A meso compound with the formula C8H18 (b) A meso compound with the formula C9H20 (c) A compound with two chirality centers, one R and the other Sarrow_forwardHexahelicene seems a poor candidate for optical activity because all its carbon atomsare sp2hybrids and presumably flat. Nevertheless, hexahelicene has been synthesized and separated into enantiomers. Its optical rotation is enormous: [a]D = 3700°.Explain why hexahelicene is optically active, and speculate as to why the rotation isso largearrow_forwardA limited number of chiral compounds having no stereogenic centersexist. For example, although A is achiral, constitutional isomer B ischiral. Make models and explain this observation. Compoundscontaining two double bonds that share a single carbon atom are calledallenes. Locate the allene in the antibiotic mycomycin and decidewhether mycomycin is chiral or achiral.arrow_forward
- Consider (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_forward(A) Which is the anti-conformer of hexane in Newman projection? (B) Which is the equivalent structure of LAM in sawhorse representation? (C) Which is the most stable conformation of pentane in Newman projection?arrow_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
- Draw the 2 chair conformers of the enantiomer of Compound XI.arrow_forwardConsider (2R,3R)-2,3-dioidobutane: (a)Draw a Fischer Projection of this structure with C1 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 bondwith C2 in front, and label your asymmetric carbons as S or R.arrow_forwardDesiganate the (R) or (S) configuration at each chirality center in the following compounds.arrow_forward
- Ketones react with alcohols to yield products called acetals. Why does the all-cis isomer of 4-tert-butyl-1,3-cyclohexanediol react readily with acetone and an acid catalyst to form an acetal, but other stereoisomers do not react? In formulating your answer, draw the more stable chair conformations of all four stereoisomers and the product acetal for each one.arrow_forward2. There are two optically inactive (and non-resolvable) forms of 1,3-di-sec-butylcyclohexane. Draw their chair conformations and explain (in less than 15 words) why the compounds are optically inactive.arrow_forwardFor each of the following compounds, draw three dimensional (perspective) diagrams of the enantiomeric pair. Indicate any pairs that would be configurationally stable (i.e. separable) at room temperaturearrow_forward
- Organic ChemistryChemistryISBN:9781305580350Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. FootePublisher:Cengage Learning