Exam 23: Introduction to Organometallic Compounds

Gillman reagents are intolerant to the presence of what functional group?

What functional group typically results when an organocopper compound (lithium organocuprate) reacts with an acid chloride?

The Stille reaction involves coupling of which pair of reagents?

Identify the best reagent for the reaction below.

What is the product in the following reaction?

Starting from vinyl chloride and ________ as the only source of carbon atoms, 1-heptene can be synthesized using a Corey-Posner/Whitesides-House coupling reaction.

Identify the product when ethylene oxide reacts with one equivalent of a Grignard reagent.

Diethyl ether is a good solvent to be used with Grignard reagents. Which of the following explanations for this fact is false?

The following synthesis is not likely to work. Which of the following explains why?

What is the product of treating styrene with the Grubbs Catalyst?

Which of the following is a boronic ester?

A total synthesis of ingenol utilized a dibromocyclopropanation via a carbene intermediate (J. Am. Chem. Soc. 2002, 124, 9726). What key type of reagent is missing from the reaction conditions?

What is the product of the following reaction sequence?

What is the product of the following ring-opening/ring-closing metathesis reaction? (J. Am. Chem. Soc. 1996, 118, 6634.)

Which of the following solvents is/are good solvents to be used in the preparation of organometallic reagents such as organolithiums and Grignard reagents? Select all that apply.

The final steps of Sammakia's total synthesis of caerulomycin C involved the reaction below (Org. Lett. 2002, 4, 2385). Draw the product.

Draw the product(s) of the following reaction:

What diene is the reactant in the following ring-closing metathesis reaction?