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Chapter 17: 51P (page 847)
The 1 H NMR chemical shifts of nitromethane, dinitromethane, and trinitromethane are at d 6.10, d 4.33, and d 7.52. Match each chemical shift with the compound. Explain how chemical shift correlates with pKa.
Nitromethane – 4.33 ppm
Dinitomethane – 6.10 ppm
Trinitromethane – 7.52 ppm
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The Reformatsky reaction is an addition reaction in which an organozinc reagent is used instead of a Grignard reagent to add to the carbonyl group of an aldehyde or a ketone. Because the organozinc reagent is less reactive than a Grignard reagent, a nucleophilic addition to the ester group does not occur. The organozinc reagent is prepared by treating an ß-bromo ester with zinc.
Describe how each of the following compounds can be prepared, using a Reformatsky reaction:
Do a retrosynthetic analysis on each of the following compounds, ending with available starting materials.
(a)
(b)
(C)
(D)
(e)
Give an example for each of the following:
(a) a -keto nitrile
(b) a -diester
(c) a-keto aldehyde
Write the mechanism for the reaction of a 1,7-diester with an alkoxide ion to form a cyclic -keto ester.
a. What carboxylic acid is formed when the malonic ester synthesis is carried out with one equivalent of malonic ester, one equivalent of 1,5-dibromopentane, and two equivalents of base?
b. What carboxylic acid is formed when the malonic ester synthesis is carried out with two equivalents of malonic ester, one equivalent of 1,5-dibromopentane, and two equivalents of base?
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