Comments on Organic Chemistry II: Benzoylation of a Polyol

17/20. If you read the experimental section you'l...

2005-08-20T07:01:31.060-04:00

17/20. If you read the experimental section you'll see that they added 6 equivalents of benzoyl chloride. Always check the experimental section to find out exactly what was done. My guess is that last benzoyl group is prevented from adding because of steric hindrance from the adjacent TBSO group.

why do you say that 3 equivalents of benzoyl chlor...

2005-08-17T11:18:23.720-04:00

why do you say that 3 equivalents of benzoyl chloride were used?

1) you still have abbreviations you didn't explain...

2005-08-17T06:36:28.933-04:00

1) you still have abbreviations you didn't explain
2) you didn't fix all the problems with Bn vs. Bz
3) you say that water was present during the reaction in pyridine - does that make sense?
4) If they were trying to stop the reaction after only 3 benzoyl groups got added, how many equivalents of benzoyl chloride should they have used?

1) I do not see that the reaction was monitored by...

2005-08-14T05:58:22.260-04:00

1) I do not see that the reaction was monitored by NMR from the article.
2) There is no benzyl chloride used in this reaction - re-read my initial comments carefully.
3) Any abbreviation you use in the scheme must be detailed in your text.

1) Make sure you understand the difference between...

2005-08-08T16:27:05.633-04:00

1) Make sure you understand the difference between a benzyl and and a benzoyl group, and which is Bz vs. Bn
1) Why is one of the alcohols left unreacted in this conversion?