C. p-Nitrobenzyl or p-Bromophenacyl Esters Cl O₂N- R Br ос R Br O₂N- R Br -R Θ Br 1.2 mmol of acid is placed in 1 mL of water in a test tube and carefully neutralized with 10% NaOH solution. Then, a tiny amount of additional acid is added to make the solution just acidic to pH paper. Then add 2 mL of 95% ethanol and 0.8 mmol of the p-nitrobenzyl chloride(PNBC)/p- bromophenacyl bromide(PBPB). Reflux the mixture for about one hour (for pNBC) or 30-40 min (for pBPB) and add small amounts of 95% ethanol if a solid separates during reflux. Allow the hot solution to cool to room temperature and the derivative to crystallize. The liquid can be removed from the crystals by using a pipette. The solid ester should be recrystallized using a minimal amount of 95% ethanol in the same reaction tube.

Organic Chemistry
9th Edition
ISBN:9781305080485
Author:John E. McMurry
Publisher:John E. McMurry
Chapter18: Ethers And Epoxides; Thiols And Sulfides
Section18.SE: Something Extra
Problem 62GP: The Zeisel method is an old analytical procedure for determining the number of methoxyl groups in a...
icon
Related questions
Question

Please provide a mechanism for the reaction with P-nitrobenzyl ester. The unknown is 3-pentanone. 

C. p-Nitrobenzyl or p-Bromophenacyl Esters
Cl
O₂N-
R
Br
ос
R
Br
O₂N-
R
Br
-R
Θ
Br
1.2 mmol of acid is placed in 1 mL of water in a test tube and carefully neutralized with 10%
NaOH solution. Then, a tiny amount of additional acid is added to make the solution just acidic to
pH paper. Then add 2 mL of 95% ethanol and 0.8 mmol of the p-nitrobenzyl chloride(PNBC)/p-
bromophenacyl bromide(PBPB). Reflux the mixture for about one hour (for pNBC) or 30-40 min
(for pBPB) and add small amounts of 95% ethanol if a solid separates during reflux. Allow the
hot solution to cool to room temperature and the derivative to crystallize. The liquid can be
removed from the crystals by using a pipette. The solid ester should be recrystallized using a
minimal amount of 95% ethanol in the same reaction tube.
Transcribed Image Text:C. p-Nitrobenzyl or p-Bromophenacyl Esters Cl O₂N- R Br ос R Br O₂N- R Br -R Θ Br 1.2 mmol of acid is placed in 1 mL of water in a test tube and carefully neutralized with 10% NaOH solution. Then, a tiny amount of additional acid is added to make the solution just acidic to pH paper. Then add 2 mL of 95% ethanol and 0.8 mmol of the p-nitrobenzyl chloride(PNBC)/p- bromophenacyl bromide(PBPB). Reflux the mixture for about one hour (for pNBC) or 30-40 min (for pBPB) and add small amounts of 95% ethanol if a solid separates during reflux. Allow the hot solution to cool to room temperature and the derivative to crystallize. The liquid can be removed from the crystals by using a pipette. The solid ester should be recrystallized using a minimal amount of 95% ethanol in the same reaction tube.
Expert Solution
steps

Step by step

Solved in 2 steps

Blurred answer
Similar questions
  • SEE MORE QUESTIONS
Recommended textbooks for you
Organic Chemistry
Organic Chemistry
Chemistry
ISBN:
9781305080485
Author:
John E. McMurry
Publisher:
Cengage Learning
EBK A SMALL SCALE APPROACH TO ORGANIC L
EBK A SMALL SCALE APPROACH TO ORGANIC L
Chemistry
ISBN:
9781305446021
Author:
Lampman
Publisher:
CENGAGE LEARNING - CONSIGNMENT