Interpretation:
The structure of compound D and E is to be proposed with the help of given data.
Concept Introduction:
Isomers are molecules which have the same number of atoms but have different arrangements of the atoms in space.
Stereoisomers are of the same molecular formula, but the arrangement of atoms in the three-dimensional orientation is different.
Enantiomers are stereoisomers whose molecules have a chiral center and the molecules are mirror images of each other.
A pair of two mirror images that are non-identical is known as a pair of enantiomers.
The objects or molecules that are superimposable with their mirror images are achiral objects or molecules. 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.
A
Degree of unsaturation of compound can be calculated using expression as:
Here, C is the number of carbon atoms, N is the number of nitrogen atoms, X is the number of halogen and H is number of hydrogen atoms.
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Chapter 5 Solutions
Organic Chemistry
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- Compound A, CH10, was found to be an optically active alcohol. Despite its apparent unsaturation, no hydrogen was absorbed on catalytic reduction over a Pd/C catalyst. On treatment of A with dilute H,SO, dehydration occurred and an optically inactive alkene B, CH4 was produced as the major product. Alkene B, on ozonolysis, gave two products. Product C, C,H,0, was shown to be an aldehyde while product D, CHg0, was shown to be a ketone. Draw the structure of compound C. • You do not have to consider stereochemistry. You do not have to explicitly draw H atoms. In cases where there is more than one answer, jtust draw one.arrow_forwardTreatment of (HOCH2CH2CH2CH2)2CO with acid forms a product of molecular formula C9H16O2 and a molecule of water. Draw the structure of the product and explain how it is formed.arrow_forward(a) Draw all stereoisomers of molecular formula C5H10Cl2 formed when (R)-2-chloropentane is heated with Cl2. (b) Assuming that products having different physical properties can be separated into fractions by some physical method (such as fractional distillation), how many different fractions would be obtained? (c) Which of these fractions would be optically active?arrow_forward
Organic ChemistryChemistryISBN:9781305580350Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. FootePublisher:Cengage Learning