Interpretation:
All the stereoisomers possible for 1,2,3-cyclopentanetriol, with their labeled chiral centers, are to be drawn. Also, the enantiomers and diastereomers that exist for the compound are to be distinguished.
Concept introduction:
Enantiomers: Two molecules that are mirror images of each other and are non-superimposable.
A meso compound is an achiral compound that has chiral centers. It tends to get superimposed on its mirror image that makes it optically inactive, although it contains two or more stereocenters. It has a
Diastereomers: Two stereoisomers that have different orientations of atoms around and are not mirror images of each other.
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Chapter 11 Solutions
Organic Chemistry
- Draw a structural formula of the S configuration of the compound shown below. • Use the wedge /hash bond tools to indicate stereochemistry where it exists. Include H atoms at chiral centers only. • Ifa group is achiral, do not use wedged or hashed bonds on it. CH3 CH3 CH;CHCHCN CH,CH,CH,CHCH,CH, CH2NH2 Draw a structural formula of the RS configuration of the compound shown below. Use the wedge /hash bond tools to indicate stereochemistry where it exists. • Include H atoms at chiral centers only. If a group is achiral, do not use wedged or hashed bonds on it. ÇIarrow_forwardOH CHзCH-CHCHCH-CHз 4-hexen-3-ol Four stereoisomers exist for 4-hexen-3-ol. Draw the structure of the isomer that has the Z configuration around the double bond and the R configuration at the chiral center. • Use the wedge/hash bond tools to indicate stereochemistry where it exists. You do not have to explicitly draw H atoms. • If a group is achiral, do not use wedged or hashed bonds on it. opy aste Previous Nextarrow_forwardDraw a 2-dimensional structure of 4,5-dibromooctane and label, with an asterisk, the tetrahedral stereo centers. What is the maximum number of stereoisomers for this molecule? Draw Fischer projections of all the potential stereoisomers of (a).arrow_forward
- Draw the correct structure for (2S,3R)-2,3-diiodopentane. Show stereochemistry clearly. To ensure proper grading, explicitly draw all four groups, including wedge/dash bonds, around a chirality center. Indicate whether the compound could exist in an optically active form. Draw (2S,3R)-2,3-diiodopentane.arrow_forward5. For the molecules below assign the stereochemical configuration of the selected tetrahedral carbon chiral centers (R, S or N (not a chiral center)) and the alkene (E, Z or N (not a stereocenter)) that are indicated by the arrows (note that you do not have to assign the configuration of every chiral center in the molecule). If the atom in question is not a chiral center or is not a stereocenter circle N for neither. b) RSN RSN HO" RSN EZ N RSN НО. H₂N HO HO OH HO OH RSN RSN CH3 НИ H3 CH₂ RSN RSN RSN EZ N RSNarrow_forwardBuild a model of each of the four stereoisomers of 2,3-dibromopentane. Why does 2,3-dibromopentane have four stereoisomers, whereas 2,3-dibromobutane has only three?arrow_forward
- 8. Two structures of Lipitor (a drug used to lower cholesterol) are shown below. (a) Determine the absolute configuration of each indicated stereocenter. Fill in the correct circle. (b) Determine if the two structures are the same compound or stereoisomers. Fill in the correct circle. (a) НО. Carbon a HO O OH Carbon a: OR OS Carbon b H N Carbon b: R OS of H Carbon c: OR OS OH OH Carbon c F Carbon d: R OS OH Carbon d (b) The two structures are: O the same compound O stereoisomersarrow_forward1. Draw all of the stereoisomers of 2,4-dichloropentane. Indicate the relationship between these stereoisomers, such as enantiomers, diastereomers, or meso compounds.arrow_forwardPredict the maximum number of stereoisomers possible for the given molecule. Но- OHarrow_forward
- Determine if 2-methylocta-4,6-dien-1-amine contains any chiral carbons. If there are chiral carbons, circle or highlight all of them. If it does not contain any chiral carbons explain why none of the carbons are chiral.arrow_forwardShown below is Streptomycin, an antibiotic medication used to treat a number of bacterial infections, including tuberculosis, plague, and endocarditis. Neomycin B has broad-spectrum antibacterial activity. Circle and label as many functional groups in these molecules as you can. Label each chiral carbon in Streptomycin. How many total stereoisomers exist for Streptomycin? Label each chiral carbon in Neomycin B. How many total stereoisomers exist for Neomycin B?arrow_forwardIdentify the stereogenic carbon in (S)- and (R)-limonene, rank the substituents around it and rationalize the assignment of their stereochemical configurations. Hint: When ranking carbons that have multiple bonds, consider the bolded carbon of C=C being connected to 2 carbons and the bolded carbon of C≡C being connected to 3 carbons.arrow_forward