Concept explainers
Interpretation: The S stereoisomers of lactic and malic acid should be drawn.
Concept introduction:The enantiomers are identical chemical compounds that have a mirror-image relationship to each other while diastereomers do not hold mirror image relationships. The former are chiral and optically active while the latter can be chiral or achiral. Together enantiomers and diastereomers constitute the total stereoisomers of any chiral compound.
In order to assign absolute configuration of R and S, Cahn − Ingold − Prelog rules are used and the first step is to assign the priority order on the basis of
Want to see the full answer?
Check out a sample textbook solutionChapter 8 Solutions
Organic Chemistry: Structure and Function
- The first step in the metabolism of glycerol, formed by digestion of fats, is phosphorylation of the pro-R—CH2OH group by reaction with adenosine triphosphate (ATP) to give the corresponding glycerol phosphate plus adenosine diphosphate (ADP). Show the stereochemistry of the product.arrow_forwardTreatment of -D-glucose with methanol in the presence of an acid catalyst converts it into a mixture of two compounds called methyl glucosides (Section 25.3A). In these representations, the six-membered rings are drawn as planar hexagons. (a) Propose a mechanism for this conversion and account for the fact that only the OH on carbon 1 is transformed into an OCH3 group. (b) Draw the more stable chair conformation for each product. (c) Which of the two products has the chair conformation of greater stability? Explain.arrow_forwardThe lactic acid that builds up in tired muscles is formed from pyruvate. If the reaction occurs with addition of hydrogen to the Re face of pyruvate, what is the stereochemistry of the product?arrow_forward
- 8. Identify the stereochemical relationship between the structural pairs shown below as (A) identical structures that are not meso; (B) identical structures that ARE meso; (C) structures that are enantiomers; or (D) structures that are diastereomers. a) b) H3C c) CH3 Br H. CH3 Br Br CH3 H. CI Holl H Cill Cl- CH3 Br H. CI CH3 HO. H. H3C Cl H3C- H- H. CH3 Cl a) b) c) 9. Identify the stereochemical relationship between the structural pairs shown below as (A) identical structures that are not meso; (B) identical structures that ARE meso; (C) structures that are enantiomers; or (D) structures that are diastereomers. a) b) c) CH2CH3 NH2 HO CH3 H3C. CH3 Cl HO H;C CH2CH3 F. F H;C. CI H H,N -CH3 CH3 NH2 H3C Br H2N C1 H3C CH3 CH3 H;CH,C- Cl F H. H Br CH,CH3 CH3 a) b) c)arrow_forwardCitrate synthase, one of the enzymes in the series of enzyme-catalyzed reactions known as the citric acid cycle, catalyzes the synthesis of citric acid from oxaloacetic acid and acetyl-CoA. If the synthesis is carried out with acetyl-CoA that contains radioactive carbon (14C) in the indicated position , the isomer shown here is obtained. a. Which stereoisomer of citric acid is synthesized: R or S? b. If the acetyl-CoA used in the synthesis contains 12C instead of 14C, will the product of the reaction be chiral or achiral?arrow_forwarda Draw the structure of the intermediate (I) for the reaction below. Hg(O2CCH3)2 NaBH4 Product CH;OH H3C • Use the wedge/hash bond tools to indicate stereochemistry where it exists. If the reaction produces a racemic mixture, just drawv one stereoisomer.arrow_forward
- 1. Trehalose is a disaccharide that can be obtained from fungi, sea urchins and insects. Acid hydrolysis of trehalose yields only D-glucose. Trehalose is hydrolysed by α-glucosidase and not by β-glucosidase enzymes. Methylation of trehalose followed by hydrolysis yields two molar equivalents of 2,3,4,6-tetra-O-methyl-D-glucopyranose.From the following experimental data, deduce the structure of trehalose.What will be the effect of trehalose on Fehling’s solution? 2.Suggest a test you will use to show that a given food substance contains proteinarrow_forwardHow many chirality centers are contained in (a) the aldotetrose and (b) the ketopentose just given below? How many stereoisomers would you expect from each general structure? CH,OH C=0 Н-С—ОН Н-С—ОН Н—С—ОН Н—С—ОН ČH,OH CH,OH Aarrow_forwardDisregarding stereoisomers, how many different enols can the β-diketone CH3COCH2COCH2CH3 form?arrow_forward
- 5. Given the following structure: (a) Draw all the stereoisomers; CH2 OH (b) Identify all of the enantiomeric and diastereomeric pairs; (c) Assign R or S configuration at each asymmetric carbon for each structure. Justify your assignments for the original structure (above).arrow_forwardWhat are products formed from the below reaction?Draw the stereoisomers and name them.(Hint: There are two different constitutional isomers and each constitutional isomer has 2nstereoisomers.arrow_forwardPlease fill in the missing reactants, reagents or products in the following reactions. Indicate relative stereochemistry where it is necessary CI j)arrow_forward
- Organic ChemistryChemistryISBN:9781305580350Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. FootePublisher:Cengage Learning