Concept explainers
Interpretation:
The structural formulas for all the stereoisomers of
Concept introduction:
The moleculesthat are nonsuperimposable or not identical with their mirror images are known as chiral molecules.
A pair of two mirror images that are nonidentical is known as enantiomers, which are optically active.
The objects or moleculesthat 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 that are nonsuperimposable on each other and not mirror images of each other are known as diastereomers.
Stereoisomers that are mirror images of each other are enantiomers.
Achiral molecules that contains chiral centres and have a plane of symmetry are called meso compounds.
Meso compounds are optically inactive.
In double bond or cyclic compounds, if two same
If the two functional groups are present on the different sides of the double bond or cyclic compound, the given compound can be labeled as Trans.
Cis-trans isomerism exists in the compounds in which similar groups are present on the adjacent carbon atoms.
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EBK ORGANIC CHEMISTRY
- According to IUPAC nomenclature rules, the naturally occurring form of menthol can also be called (1R, 2S, 5R)-2-isopropyl-5- methylcyclohexanol. (a) Draw the bond-line structure of the enantiomer of this compound, including wedged and hashed bonds where appropriate to show stereochemical configuration. (b) Draw the chair conformation of this structure and perform a ring flip operation. Circle the most stable chair conformer. Briefly explain why it is the most stable.arrow_forward2.35 Write a structural formula for each of the following compounds: (a) 6-Isopropyl-2,3-dimethylnonane (b) 4-tert-Butyl-3-methylheptane (c) 4-Isobutyl-1,1-dimethylcyclohexane (d) sec-Butylcycloheptane (e) Cyclobutylcyclopentanearrow_forwardConsider 1-bromo-2-methylpropane and draw the following. Q) The staggered conformation(s) of highest energyarrow_forward
- Consider 1-bromopropane, CH3CH2CH2Br. (a) Draw a Newman projection for the conformation in which CH3 and -Br are anti (dihedral angle 180°). (b) Draw Newman projections for the conformations in which - CH3 and -Br are gauche (dihedral angles 60° and 300°). (c) Which of these is the lowest energy conformation? (d) Which of these conformations, if any, are related by reflection?arrow_forwardFor each of the following molecular formulas, determine the number of elements of unsaturation,and draw three examples.(a) C4H4Cl2 (b) C4H8Oarrow_forwardCompound X, C,4H12Br2, is optically inactive. On treatment with strong base, X gives hydrocarbon Y, C14H10: Compound Y absorbs 2 equivalents of hydrogen when reduced over a palladium catalyst to give z (C14H14) and reacts with ozone to give one product, benzoic acid (C,Hg02). Draw the structure of compound Z. • Use the wedge/hash bond tools to indicate stereochemistry where it exists. • Ignore alkene stereochemistry. • If more than one structure fits the description, draw them all. • Draw one structure per sketcher. Add additional sketchers using the drop-down menu in the bottom right corner. • Separate structures with + signs from the drop-down menu. ChemDoodlearrow_forward
- Consider 1-bromo-2-methylpropane and draw the following. (a) The staggered conformation(s) of lowest energy (b) The staggered conformation(s) of highest energyarrow_forwardFollowing is a planar hexagon representation of L-fucose, a sugar component of the determinants of the A, B, O blood group typing. For more on this system of blood typing, see Chemical Connections: A, B, AB, and O Blood Group Substances in Chapter 25. (a) Draw the alternative chair conformations of L-fucose. (b) Which of them is more stable? Explain.arrow_forwardUsing what you know about the conformational energetics of substituted cyclohexanes, predict which of the two decalin isomers is more stable. Explain your reasoning.arrow_forward
- Refer the structure below: CH3 CH3 CH3 CH3 Compound I Compound II (i) Are the above cyclohexane derivatives cis- or trans-isomer? (ii) Redraw the structure in chair conformation and identity which of these the most and the least stable.arrow_forward2A2: Apply the concepts of stereocenters, chirality, asymmetry, and the CIP Rules to label enantiomers/ diastereomers and R/S or E/Z absolute configurations. These two (2) structures have ambiguous configurations. Provide a wedge and dash structure for the indicated configurational isomer. In your response, keep the overall structural orientation the same as given. In addition, label all alkenyl FGs as either E or Z in both structures by showing your work. & H3 C CH3 (R, R, R,) H3CO. H3CO CH3 (S, S, S) CH3 OCH 3 OCH 3arrow_forwardDraw all the possible conformations for the compounds below. Identify the most stable conformation for each of the following compounds. Give reason(s) for your answer. (i) 1-hydroxy-2,3-dichlorocyclohexane (ii) 1-ethyl-2-methylcyclohexanearrow_forward
- Organic ChemistryChemistryISBN:9781305580350Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. FootePublisher:Cengage Learning