Assign the appropriate designation of configuration (R or S) to the stereocenter in each of the following enantiomers. (Hint: Regarding cyclic structures containing stereocenters, treat the ring as if it were two separate substituents that happen to be attached to each other at the far end of the molecule-look for the first point of difference, just as you would for acyclic structures.) H,C H (b) (d) OH OH OH (e) (f) CI (h) OH HO HC H HCH () CH, H. OCH *NH,

Assign the appropriate designation of configuration (R or S) to the stereocenter in each of the following enantiomers. (Hint: Regarding cyclic structures containing stereocenters, treat the ring as if it were two separate substituents that happen to be attached to each other at the far end of the molecule-look for the first point of difference, just as you would for acyclic structures.) H,C H (b) (d) OH OH OH (e) (f) CI (h) OH HO HC H HCH () CH, H. OCH *NH,

Organic Chemistry

8th Edition

ISBN:9781305580350

Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote

Publisher:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote

Chapter2: Alkanes And Cycloalkanes

Section: Chapter Questions

Problem 2.62P: Following is a planar hexagon representation of L-fucose, a sugar component of the determinants of...

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4. Draw all possible stereoisomers of the following compounds. Assign the appropriate absolute (R/S) or geometric (E/Z) configuration to each of the stereoisomers (or double bonds) and label pairs enantiomers, diastereomers and meso compounds. (a) CH3CHBRCHOHCH3 (c) CH3CH=C(Br)CH=CHCI (e) CH3CH₂CHOHCHOHCH2CH3 (g) OH НО... CI (h) H3C Br (b) CH3CHBRCHBRCH ₂Br (d) CH3CH(C6H5)CHOHCH3 (f) CH₂(OH)CH2-CH(OH)CH=CHOH CH3 (1) Br HS Br
If molecules A and B are isomers of each other, then what kinds of isomers could they be (i.e., enantiomers, diastereomers, or constitutional isomers) under each of the following conditions?(a) Both molecules have the same IHD.(b) Molecule A has a ring but molecule B does not.(c) Molecules A and B contain different functional groups.(d) Molecules A and B share exactly the same functional groups.(e) Molecule A has a plane of symmetry but molecule B does not.
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).
Determine whether each of the following names describes a single stereoisomer unambiguously. For each one that does,rewrite the name using the R and S designations for the chiral centers if appropriate. (a) cis-1,2-difluorocyclohexane;(b) trans-1,2-difluorocyclohexane; (c) trans-1,4-difluorocyclohexane; (d) cis-1-chloro-2-fluorocyclohexane; (e) trans-1,4-dimethylcycloheptane
Identify 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.
Coibacin B (shown below) is a natural product that exhibits potent anti-inflammatory activity and potential activity in the treatment of leishmaniasis, a disease caused by certain parasites (Org. Lett. 2012, 14, 3878-3881): (a) Assign the configuration (R or S) of each chirality center (labeled A to C) in coibacin B. (b) Identify the number of possible stereoisomers for this compound, assuming that the geometry of the alkenes are fixed. Choices are given below and write the CAPITAL LETTER of your choice. A. 2 В. 4 С. 8 D. 16 ANSWERS: (a) A. В. C. (b)
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 stereoisomers
Draw all of the possible stereoisomers of the compound shown. Group them as enantiomeric pairs, or indicate any meso compounds. Label all stereocenters with the absolute stereochemistry (R or S).
(A)Menthol, used to flavor various foods and tobacco, is the most stable stereoisomer of 2-isopropyl-5-methylcyclohexanol. Draw its most stable conformation. Is the hydroxyl group cis or trans to the isopropyl group? To the methyl group? (b) Neomenthol is a stereoisomer of menthol. That is, it has the same constitution but differs in the arrangement of its atoms in space. Neomenthol is the second most stable stereoisomer of 2-isopropyl-5methylcyclohexanol; it is less stable than menthol but more stable than any other stereoisomer. Write the structure of neomenthol in its most stable conformation.
For the following pairs of compounds, indicate the relationship (identical compounds, enantiomers, diastereomers, or constitutional isomers). The same answer can be used more than once. (b) H (a) H HO COME MeO2C OH NH2 NH2 H2N H -NH2 H. MeO2C H HO' `CO,Me H Но, H (c) CH2CH3 (d) CH3 Br Br -CH2CH3 Br H- Br, H EH H EH но— H;C CH3 H3C+Br H- -Br CH3 H CH3
Identify the specific relationship between each of the following pairs of molecules (i.e., either same, constitutional isomers, enantiomers, diastereomers, conformers, or unrelated). CH3 (c) Br CH3 (а) CI OH (b) Br НО Br, CH3 Br ОН CI (f) Br OCH3 (d) CH3 (e) CH3 CH3 CH3 ОН OCH3 Br H ОН
9. Which compound reacts with both NaBH and H/Pt to produce the same product? A) 1 4 2 B) II III CHO ||| D) None of these 10. Reduction of a carbonyl to produce a stereogenic center A) occurs with the formation of both diastereomers. B) occurs with the formation of both enantiomers. (C) occurs stereospecifically yielding a single isomeric product. D) none of these. MgBr 11. Which reagent would you use to produce (S)-1-phenylethanol from phenyl methyl ketone (acetophenone)? 12. A) S-CBS reagent B) R-CBS reagent C) NaBH +S-CBS reagent 4 D) NaBH + R-CBS reagent 4 An aldehyde can be produced by the reaction of the compound shown with which reagent? A) B) || D IV OCH3 I) H₁/Pt III) LiAlH4 II) NaBH4 IV) DIBAL-H 13. LiAlH reacts with which of the following? 4 A) | H .0 CI 0 EtO. 0 B) C) III D) All of these I II III