(a)
Interpretation:The natural products indicated should be identified as either chiral or achiral.
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.
Four kinds of symmetry elements that may be present are tabulated as follows:
Presence of any symmetry element makes molecule achiral and optically inactive.
(b)
Interpretation: The three molecules that represent enantiomers of
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.
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Chapter 5 Solutions
Organic Chemistry: Structure and Function
- Consider 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_forward12. 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) Draw and label the possible stereochemistry (R/S) of all potential products from cis and trans addition of chlorine to the double bond of cis-2-butene. (Hint see Expt. 3) Clearly indicate meso, enantiomer and diastereomer relationships. CH3 H CH3 CH3 CH3 X- H H cis trans tr H ||||| H *arrow_forward
- One of the isomers of 1,2,3,4,5,6-hexahydroxycyclohexane, called myo-Inositol, acts as a growth factor in both animals and microorganisms. Draw the most stable chair conformation of myo-Inositol (Note: account the wedge and dash projection). Draw the most stable cis-trans stereoisomer of myo-Inositol. OH HO ОН HO "OH ОНarrow_forwardConsider the reaction between (1S,3S)‑1‑chloro‑3‑methylcyclopentane and methanethiol in the presence of sodium hydroxide. (a) Draw the organic product and clearly indicate stereochemistry by showing the hydrogen on the chirality centers and using wedge and dash bonds. (b) Then analyze the stereochemistry of the product. racemic chiral achiral (1R, 3S) (1R, 3R) (1S, 3S)arrow_forward2A2: Apply the concepts of stereocenters, chirality, asymmetry, and the CIP Rules to label enantiomers/ diastereomers and R/S or E/Z absolute configurations. These two (2) structures have ambiguous configurations. Provide a wedge and dash structure for the indicated configurational isomer. In your response, keep the overall structural orientation the same as given. In addition, label all alkenyl FGs as either E or Z in both structures by showing your work. & H3 C CH3 (R, R, R,) H3CO. H3CO CH3 (S, S, S) CH3 OCH 3 OCH 3arrow_forward
- (a) Describe the molecular geometry expected for 1,2,3-butatriene (H2C=C=C=CH2). (b) Two stereoisomers are expected for 2,3,4-hexatriene (CH3CH=C=C=CHCH3). What should be the relationship between these two stereoisomers?arrow_forward9. For 3-fluoro-2-methylpentane, draw the Newman projection for the: (a) lowest energy conformation; (b) highest energy conformation, looking down the C-2 and C-3 bond length. You can use the following as shorthand: Me = methyl; Et = ethyl. (a) (b)arrow_forwardConsider 1-bromopropane, CH3CH2CH2Br. (a) Draw Newman projections for the conformations in which -CH3 and -Br are gauche (dihedral angles 60° and 300°).arrow_forward
- 5. 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_forwardassign 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.arrow_forwardUsing solid and dashed wedges, draw the structure of (1S, 2S, 4R, 5R)-1,5-dibromo-2,4- dichlorocyclohexane, then draw the most stable conformer.arrow_forward