Question
An explicit aqueous acid workup is required after reactions using these compounds since they are incompatible with water. For 10 points each:
[10e] Name these strong nucleo·philes composed of organo·magnesium halides.
ANSWER: Grignard (“grin-yar”) reagents
[10m] Grignard reagents react with ketones to form what specific products? Your answer [emphasize] must include a substitution pattern.
ANSWER: tertiary alcohols [or 3° alcohols; prompt on alcohols]
[10h] Description acceptable. Grignard reagents also form tertiary alcohols when they react with esters or nitriles, but only if they are provided to the reaction in this way. N-butyl-lithium must also be supplied to the Shapiro reaction in this way.
ANSWER: at least two-fold stoichiometric excess [or at least two stoichiometric equivalents of Grignard reagent must be added; or descriptions of adding at least twice as much or adding double; accept any number greater than or equal to two, such as three-fold, in place of “two”; prompt on molar excess or stoichiometric excess by asking “how much?”] (The first Grignard equivalent reduces the ester or nitrile to a ketone.)
Data
| Team | Opponent | Part 1 | Part 2 | Part 3 | Total |
|---|---|---|---|---|---|
| WUSTL B | Yale B | 10 | 10 | 0 | 20 |