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Reaction of Compound 1 (C3H9SBr) with one molar equivalent of sodium acetylide ( HC=CNa) in CH2C12 (this is a polar aprotic solvent, it does NOT participate in the mechanism for this reaction) leads to Compound 2, C,H10S and sodium bromide (NaBr). C4HgSBr HCECNA HC=C + NaBr Compound 1 CH,Cl2 CH3 C6H10S Compound 2 a) Did this substitution reaction proceed via SN1 or Sn2 mechanism? Justify your answer. b) Draw the structure of Compound 1(with proper stereochemistry) and label R/S where necessary and state if Compound 1 is optically active. c) Label R/S where necessary for Compound 2 and state if Compound 2 is optical activity.

Reaction of Compound 1 (C3H9SBr) with one molar equivalent of sodium acetylide ( HC=CNa) in CH2C12 (this is a polar aprotic solvent, it does NOT participate in the mechanism for this reaction) leads to Compound 2, C,H10S and sodium bromide (NaBr). C4HgSBr HCECNA HC=C + NaBr Compound 1 CH,Cl2 CH3 C6H10S Compound 2 a) Did this substitution reaction proceed via SN1 or Sn2 mechanism? Justify your answer. b) Draw the structure of Compound 1(with proper stereochemistry) and label R/S where necessary and state if Compound 1 is optically active. c) Label R/S where necessary for Compound 2 and state if Compound 2 is optical activity.

Organic Chemistry
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 16.42P: When cis-2-decalone is dissolved in ether containing a trace of HCl, an equilibrium is established...
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d) You are conducting this reaction in the lab and your partner comes in and accidently adds H20 instead of CH2Cl2. Two new Compounds 3 and 4, both with same molecular formula (C4H10SO), are made. Draw the new products and state if the solution containing the new products would be optically active or inactive.
Transcribed Image Text:d) You are conducting this reaction in the lab and your partner comes in and accidently adds H20 instead of CH2Cl2. Two new Compounds 3 and 4, both with same molecular formula (C4H10SO), are made. Draw the new products and state if the solution containing the new products would be optically active or inactive.
3) Reaction of Compound 1 (C3H9SB1) with one molar equivalent of sodium acetylide ( HC=CNa ) in CH2CI2 (this is a polar aprotic solvent, it does NOT participate in the mechanism for this reaction) leads to Compound 2, C6H10S and sodium bromide (NaBr). C4H9SBr HCECNA S- HCEC- + NaBr Compound 1 CH,Cl, CH3 C6H10S Compound 2 a) Did this substitution reaction proceed via SN1 or Sn2 mechanism? Justify your answer. b) Draw the structure of Compound 1(with proper stereochemistry) and label R/S where necessary and state if Compound 1 is optically active. c) Label R/S where necessary for Compound 2 and state if Compound 2 is optical activity.
Transcribed Image Text:3) Reaction of Compound 1 (C3H9SB1) with one molar equivalent of sodium acetylide ( HC=CNa ) in CH2CI2 (this is a polar aprotic solvent, it does NOT participate in the mechanism for this reaction) leads to Compound 2, C6H10S and sodium bromide (NaBr). C4H9SBr HCECNA S- HCEC- + NaBr Compound 1 CH,Cl, CH3 C6H10S Compound 2 a) Did this substitution reaction proceed via SN1 or Sn2 mechanism? Justify your answer. b) Draw the structure of Compound 1(with proper stereochemistry) and label R/S where necessary and state if Compound 1 is optically active. c) Label R/S where necessary for Compound 2 and state if Compound 2 is optical activity.
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