]>90% e.e.TSOH (cat.), CH,Cl2then workupracemicноmostly one diastereomer]5:1 diastereomer mixproduct after these transformations>90% e.e.2) a) NANH2, THF, -20 °Cb) OHC-CH,CH3c) workup]racemicmostly one diastereomer3) NaH, MegSi-CI,then workup] 5:1 diastereomer mixproduct after these transformations

In the first step, the alcohol is protected as THP (tetrahydropyran ether). In the second step,…

Answered: ]>90% e.e. racemic 1) TSOH (cat.),…

Chemistry

10th Edition

ISBN:9781305957404

Author:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste

Publisher:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste

Chapter1: Chemical Foundations

Section: Chapter Questions

Problem 1RQ: Define and explain the differences between the following terms. a. law and theory b. theory and...

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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
2.) Which is a pair of enantiomers? CH3 H3C CI CH;CH2CH3 CH3 CH3 CH;CH;CH3 H3C CI CH;CH2CH; II II CH,CI CH;CH2CH3 H3C CI CH;CH2CH3 IV V A. I& II and III & IV В. I & II С. II & IV D. IV & V
4. Study the reactions listed below and decide whether the products are going to be a mixture of enantiomers, diastereomers, or neither. i. ii. iii. iv. V. Reaction Cl₂₁₂ H₂ CC14 Pt H₂O* Br₂ H₂O CCL4, hv NBS HBr Products & Mixture Diastereomers
chem 534 cha Hư OAC H please show stereochemistry H₂ COCH ? H CO₂CH3 O Ac 2. + ? hv 9 40°C 3. H₂ C 4. 0°C Catq Q-0 + [6+4] NGC ?. لك 5. [ V-CO₂CH3 + II NCCN [4+2] C6H5 6. 2 C6H5
& & CI OI OI and II O III || ON "Cl Which of the above has 2 stereogenic centers with both R configurations? ..= J. IV
С. (1) BH3 (2) H,O,. H,O, NaOH Product is (circle one) i. A racemic mixture ii. A single enantiomer, iii. Achiral or meso D. txt. CI Ci
H OMe OMe H (this enantiomer) a) BH, THF b) H₂O₂, NaOH then workup >90% e.e. racemic mostly one diastereomer <5:1 diastereomer mix product after these transformations
C. IDENTIFYING STEREOISOMERS: Label each pair of molecules below as enantiomers, diastereomers or identical CO₂H HO HC но-- н H -.Н CH3 OH CH₂OH HO™ H₂OC H₂C Н-- HO Н CH3 OHH CH₂OH HOC-... HOCH₂. H OH H OH HO H CHO COzH ОНС но с HO H COzH Н ОН НО Н CH₂OH
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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)
Give the major organic product(s) of the following. Include stereochemistry when applicable. 1) Nal Br a) 2) NaCN, acetone 1) NaOC(CH3)3, heat d Br 2) BH₂ THF; 3) H,O,, NaOH(aq) b) c) d) c) 2) KOC(CH3)3, heat Copyright University of California Merced 2022 Br 1) NaOH, heat 2) MCPBA 1) KOC(CH3)3, heat 2) H3O+
Describe the relationship of the following pairs of molecules as identical, enantiomers, diastereomers, or constitutional isomers. Br Ме, Н Me CI Me i. CI Br H Me H CI, Et Me CI Et Et. ii. Me Et Me CI Mee CI iii. none of the other answer choices are correct O i. = diastereomers; ii. = identical; iii. = enantiomers i. = diastereomers; ii. = constitutional isomers; iii. = diastereomers i. = enantiomers; ii. = constitutional isomers; iii. = diastereomers O i. = enantiomers; i. = identical; iii. = diastereomers

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