Concept explainers
(a)
Interpretation:
The experimental conditions required to bring about the given conversion reaction has to be described.
Concept Introduction:
Treatment of an
Example:
(b)
Interpretation:
Check whether the given compound Rimantadine is chiral or not and the number of stereoisomers possible for the compound has to be determined.
Concept Introduction:
Enantiomers: These are stereoisomers that are not superimposable mirror images of each other and the configurations at all stereo genic centers are exactly opposite.
Chiral center: A chiral center is defined as the tetrahedral carbon atom in an organic molecule that is connected to four non-identical groups/substituents. It is sometimes known as a stereo genic center.
Chirality: The geometric property of molecules where the structure of the molecule and its mirror image are not superimposable is known as chirality. Chiral molecules are optically active and they can rotate the plane polarized light.
The number of stereoisomers possible for a compound can be determined using the below mentioned equation.
Treatment of an aldehyde or ketone with ammonia or an amine in the presence of a reducing agent (like
Example:
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Organic Chemistry
- 12. Natural (2)-menthol, the essential oil primarily responsible for the flavor and aroma of peppermint, is the IR,25,5R-stereoisomer. (a) Identify (2)-menthol from the structures you drew for Problem 50, part (b). (b) Another of the naturally occurring diastereomers of menthol is (1)-isomenthol, the 1S 2R5R- stereoisomer. Identify (1)-isomenthol among your structures. (c) A third is (1)-neomenthol, the 15.25,SR-compound. Find (1)-neomenthol among your structures. (d) Based on your understanding of the conformations of substituted cyclohexanes (Section 4-4), what is the stability order (from most stable to least) for the three diastereomers, menthol, isomenthol, and neomenthol?arrow_forwarda) When (Z)-3-methylhex-3-ene undergoes hydroboration–oxidation, two isomeric products are formed. Give their structures, and label each asymmetric carbon atom as (R) or (S). What is the relationship between these isomers?arrow_forward1. (a) Describe aromaticity, Kekule structure and resonance structure for benzene. (b) Why is benzene more stable than aliphatic alkenes?arrow_forward
- (a) Draw the products of molecular formula C3H4Cl2, including stereoisomers, formed when chlorocyclopropane is heated with Cl2. (b)Assuming that compounds that have different physical properties are separable, how many fractions would be present if the mixture of products were distilled using an efficient fractional distillation? (c) How many fractions would be optically active?arrow_forwardIf either of the following molecules has a stereogenic carbon (chirality center), give structures for both of the enantiomers. (a) 2-bromopropane (b) 2-bromobutanearrow_forward(a) Write the structures of the following compounds and mark them as chiral or achiral. 4 (i) 2-Bromopentane (ii) 3-Bromopentane (iii) 1-Bromo-2-methylbutane (iv) 2-Chloro-3-methylbutane (b) Identify the asymmetric carbon in the chiral compounds. (c) Write the structure of the other enantiomer of the chiral compounds.arrow_forward
- The shrub ma huang (Section 5.4A) contains two biologically activestereoisomers—ephedrine and pseudoephedrine—with two stereogeniccenters as shown in the given structure. Ephedrine is one component ofa once-popular combination drug used by body builders to increaseenergy and alertness, whereas pseudoephedrine is a nasaldecongestant.a.) Draw the structure of naturally occurring (−)-ephedrine, which has the1R,2S configuration.b.) Draw the structure of naturally occurring (+)-pseudoephedrine, whichhas the 1S,2S configuration.c.) How are ephedrine and pseudoephedrine related?d.) Draw all other stereoisomers of (−)-ephedrine and (+) pseudoephedrine, and give the R,S designation for all stereogeniccenters.e.) How is each compound drawn in part (d) related to (−)-ephedrine?arrow_forward1 Provide the IUPAC name of the following compounds, with clear indication of stereochemistry for stereocenters and alkene. (a) (b) Br (c) Me. (d) Mearrow_forwardDraw a three-dimensional structure for each compound, and star all asymmetric carbon atoms. Draw the mirror image for each structure, and state whether you have drawn a pair of enantiomers or just the same molecule twice. Build molecular models of any of these examples that seem difficult to you. (a) ОН (b) (c) NH, ОН СH—CH—СООН | pentan-2-ol pentan-3-ol alanine (d) 1-bromo-2-methylbutane (e) chlorocyclohexane (f) cis-1,2-dichlorocyclobutane (h) (i) H CH; "H H. H CH, Harrow_forward
- Compound 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_forwardConsider 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_forwardDHA is a fatty acid derived from sh oil and an abundant fatty acid in vertebrate brains. Hydrogenation of DHA forms docosanoic acid [CH3(CH2)20CO2H] and ozonolysis forms CH3CH2CHO, CH2(CHO)2 (ve equivalents), and HCOCH2CH2CO2H. What is the structure of DHA if all double bonds have the Z conguration?arrow_forward
- Organic ChemistryChemistryISBN:9781305580350Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. FootePublisher:Cengage Learning