Concept explainers
Interpretation: All possible constitutional and stereoisomers for a compound of molecular formula
Concept introduction: A compound exhibits number of stereoisomers when it contains more than one stereogenic centers. The maximum number of stereoisomers a compound with
Want to see the full answer?
Check out a sample textbook solutionChapter 5 Solutions
Organic Chemistry
- Draw all possible constitutional isomers and stereoisomers for acompound of molecular formula C6H12 having a cyclobutane ring andtwo methyl groups as substituents. Label each compound as chiral orachiral.arrow_forwardConsider the following pairs of structures. Identify the relationship between them by describing them as representing enantiomers, diastereomers, constitutional isomers, or two molecules of the same compound. H H3C" CH3 Br Hitm Br enantiomers constitutional isomers diastereomers H B H F F two molecules of the same compound CH3 H Ba CH3arrow_forwardWhat is true about the relationship between the following compounds? CH3 CH3 CH; CH; CH3 CH3 A В O All three are stereoisomers of each other. OA and B are the same compound while C is a stereoisomer. All three are the same compound. A and B are the same while C is a conformer, all of the same compound . O A and C are the same while B is a stereoisomer.arrow_forward
- OH 1. Consider this compound: CH;CH2CHCH,CHCH2CH3 ČH3 a) How many chiral carbons does this compound have? b) What is the maximum number of stereoisomers that could exist for this compound? Show how you arrived at your answer.arrow_forward1) The following compound, whose central ring is referred to as a 1,2,4-trioxane, is an anticancer agent that demonstrates activity against canine osteosarcoma. Assign the configuration of each chiral center and then draw all possible stereoisomers of this compound, showing the specific stereochemical relationship between each of your drawings. H -OH O-N O-Oarrow_forwardDraw 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_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_forwardA compound that contains two different stereocenters can exist as four optically active stereoisomers. The flying wedge representations of the four stereoisomers are given below: ÇOOH COOH ÇOOH COOH H-C-OH HO-C-H H-C-OH HO-C-H H-C-OH HO-C-H HO-C-H H-C-OH CH3 ČH3 ČH3 ČH3 II IV What is the relationship between: III and IV? II and IV? П аnd III) 96.I and II? 97.I and IV? 98.I and III?arrow_forwardConformational studies on ethane-1,2-diol (HOCH2¬CH2OH) have shown the most stable conformation about the central C¬C bond to be the gauche conformation, which is 9.6 kJ/mol (2.3 kcal/mol) more stable than the anti conformation. Draw Newman projections of these conformers, and explain this curious result.arrow_forward
- Name and draw structural formulas for the eight constitutional isomeric alcohols with molecular formula C5H12O. Classify each alcohol as primary, secondary, or tertiary. Which are chiral?arrow_forwardDraw all possible stereoisomers of the following compound (there are four of them). You need to consider both the chiral carbon and the double bond CH;CH=CHCH(CI)CH3arrow_forwardDraw the three constitutional isomers having molecular formula C7H14 that contain a ve-membered ring and two methyl groups as substituents. For each constitutional isomer that can have cis and trans isomers, draw the two stereoisomers.arrow_forward
- Organic ChemistryChemistryISBN:9781305580350Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. FootePublisher:Cengage LearningIntroduction to General, Organic and BiochemistryChemistryISBN:9781285869759Author:Frederick A. Bettelheim, William H. Brown, Mary K. Campbell, Shawn O. Farrell, Omar TorresPublisher:Cengage Learning