4. (3) For each of the following reactions, fill in the missing reagents from the list provided for the formation of the product shown. Sequential steps, if necessary, should be numbered. Reagents may be used more than once. Reagent List: Lit NaH NaNH2 Na+ H,C-S-CI HBr PBr3 H20 Br2 LI-CH3 но NaOH Br-CH3 KBr (HOAC) (pyridine) (LDA) (MSCI) но Br. Br

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
Chapter16: Aldehydes And Ketones
Section: Chapter Questions
Problem 16.45P: The following bicyclic ketone has two -carbons and three -hydrogens. When this molecule is treated...
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4. (3) For each of the following reactions, fill in the missing reagents from the list provided for the
formation of the product shown. Sequential steps, if necessary, should be numbered. Reagents
may be used more than once.
Reagent List:
Lit
NaH NaNH2
Na+
H,C-S-CI
HBr
PBr3
H20
Br2
Li-CH3
но
NaOH
Br-CH3
KBr
(HOAC)
(pyridine)
(LDA)
(MSCI)
но
Br. Br
5. (5) In reaction A, the product was determined to be racemic (both enantiomers were formed).
(a) Propose a curved arrow mechanism for reaction A that accounts for this observation.
(b) Predict the product for reaction B where conditions now use a different chloride source.
b)
H-CI
но
CI
1. LICI
2. HCI
reaction A
reaction B
Transcribed Image Text:4. (3) For each of the following reactions, fill in the missing reagents from the list provided for the formation of the product shown. Sequential steps, if necessary, should be numbered. Reagents may be used more than once. Reagent List: Lit NaH NaNH2 Na+ H,C-S-CI HBr PBr3 H20 Br2 Li-CH3 но NaOH Br-CH3 KBr (HOAC) (pyridine) (LDA) (MSCI) но Br. Br 5. (5) In reaction A, the product was determined to be racemic (both enantiomers were formed). (a) Propose a curved arrow mechanism for reaction A that accounts for this observation. (b) Predict the product for reaction B where conditions now use a different chloride source. b) H-CI но CI 1. LICI 2. HCI reaction A reaction B
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