(1) (2) COOH A (CaH14O5) C (CH1804) HOOC (R)-Malic acid F (C,H,OBr2) A bromoepoxide Steps/Reagents 1. CH,CH,OH, H* 2. dihydropyran, H* 3. LIAIH4, then H0 4. TSCI, pyridine 5. NaBr, DMSO 6. H20, CH;COOH 7. КОН

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
Chapter14: Mass Spectrometry
Section: Chapter Questions
Problem 14.37P
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Please label all the steps and reagents with their corresponding letter. Thanks!
он
(2)
A (C3H1405)
(3)
B
(1)
COOH
C (C9H1804)
HOOC
(R)-Malic acid
(5)
(7)
F (C,HOBr2)
A bromoepoxide
Steps/Reagents
1. CH;CH2OH, H*
2. dihydropyran, H*
3. LIAIH4, then H20
4. TSCI, pyridine
5. NaBr, DMSO
H20, CH;COOH
7. КОН
6.
This stereospecific synthesis, starting with enantiometrically pure (R)-malic acid, yields a bromoepoxide.
Write out the complete synthesis on a separate sheet of paper, and then draw the structure of the product of step 5.
• Use the wedge/hash bond tools to indicate stereochemistry where it exists.
• If the reaction produces a racemic mixture, draw both stereoisomers.
• Draw one structure per sketcher. Add additional sketchers using the drop-down menu in the bottom right corner.
• Separate multiple products using the + sign from the drop-down menu.
opy aste
Transcribed Image Text:он (2) A (C3H1405) (3) B (1) COOH C (C9H1804) HOOC (R)-Malic acid (5) (7) F (C,HOBr2) A bromoepoxide Steps/Reagents 1. CH;CH2OH, H* 2. dihydropyran, H* 3. LIAIH4, then H20 4. TSCI, pyridine 5. NaBr, DMSO H20, CH;COOH 7. КОН 6. This stereospecific synthesis, starting with enantiometrically pure (R)-malic acid, yields a bromoepoxide. Write out the complete synthesis on a separate sheet of paper, and then draw the structure of the product of step 5. • Use the wedge/hash bond tools to indicate stereochemistry where it exists. • If the reaction produces a racemic mixture, draw both stereoisomers. • Draw one structure per sketcher. Add additional sketchers using the drop-down menu in the bottom right corner. • Separate multiple products using the + sign from the drop-down menu. opy aste
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