Syn dihydroxylation of the compound below yields two products. Draw both products and describe their stereoisomeric relationship (i.e., are they enantiomers or diastereomers?). KMnO4, NaOH Cold
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- 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(a) Draw all stereoisomers formed by monochlorination of the cis and trans isomers of 1,2-dimethylcyclobutane drawn below. (b) How many constitutional isomers are formed in each reaction? (c) Label any pairs of enantiomers formed.Draw the structure of an alkyl bromide with molecular formula CgH13Br that fits each description: (a) a 1° alkyl bromide with one stereogenic center; (b) a 2° alkyl bromide with two stereogenic centers; (c) an achiral 3° alkyl bromide.
- (−)-Menthol is the most stable stereoisomer of 2-isopropyl-5-methylcyclohexanol and has the R configuration at the hydroxyl-substituted carbon. (a) Draw the preferred conformation of (−)-menthol. (b) (+)-Isomenthol has the same constitution as (−)-menthol. The configurations at C-1 and C-2 of (+)-isomenthol are the opposite of the corresponding chirality centers of (−)-menthol. Write the preferred conformation of (+)-isomenthol.Give the relationship between each pair of molecules below (constitutional isomers, diastereomers, enantiomers, or identical). Note that molecules may not necessarily be shown in the same conformation. 3. OH ОН ОН ОН (a) (b) ОН H OH (c) CH3 .CI (d) Н. .CH3 CH3 CH3 ОН TCI H H CI OH F Br Br ОН ОН ОН ОН (e) (f) CI ОН ОН (g) .cO NH2 NH2 .. O II S:Draw the structure of (S,S)-ethambutol, a drug used to treat tuberculosisthat is 10 times more potent than any of its other stereoisomers. (See attached)
- 11) How many possible stereoisomers does the following compound have? CH(CH32 H3CM H3C H.Ketones react with alcohols to yield products called acetals. Why does the all-cis isomer of 4-tert-butyl-1,3-cyclohexanediol react readily with acetone and an acid catalyst to form an acetal, but other stereoisomers do not react? In formulating your answer, draw the more stable chair conformations of all four stereoisomers and the product acetal for each one.Treatment 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.
- (a) Show how you would synthesize the pure (R) enantiomer of 2-butyl methyl sulfide, starting with pure (R)-butan-2-oland any reagents you need.(b) Show how you would synthesize the pure (S) enantiomer of the product, still starting with (R)-butan-2-ol and anyreagents you need.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)In some nucleophilic substitutions under SN1 conditions, complete racemization does not occur and a small excess of one enantiomer is present. For example, treatment of optically pure 1-bromo-1-phenylpropane with water forms 1-phenylpropan-1-ol. (a) Calculate how much of each enantiomer is present using the given optical rotation data. (b) Which product predominates—the product of inversion or the product of retention of configuration? (c) Suggest an explanation for this phenomenon.
