The coupling of an alkyne with an aryl halide in the presence of a palladium catalyst and triethylamine is called a Sonogashira reaction. What reactants couple to form this product?

Identify A through H

Using the given starting material, any necessary inorganic reagents and catalysts, and any carbon-containing compounds with no more than three carbons, indicate how each of the following compounds can be prepared:

a.

Using the given starting material, any necessary inorganic reagents and catalysts, and any carbon-containing compounds with no more than three carbons, indicate how each of the following compounds can be prepared:

b.

Using the given starting material, any necessary inorganic reagents and catalysts, and any carbon-containing compounds with no more than three carbons, indicate how each of the following compounds can be prepared:

c.

Using the given starting material, any necessary inorganic reagents and catalysts, and any carbon-containing compounds with no more than three carbons, indicate how each of the following compounds can be prepared:

d.

Using the given starting material, any necessary inorganic reagents and catalysts, and any carbon-containing compounds with no more than three carbons, indicate how each of the following compounds can be prepared:

e.

Using the given starting material, any necessary inorganic reagents and catalysts, and any carbon-containing compounds with no more than three carbons, indicate how each of the following compounds can be prepared:

f.

What alkyl halide reacts with lithium divinylcuprate [(CH₂=CH)₂CuLi] for the synthesis of each of the following compounds?

a.

b.

What alkyl halide reacts with lithium divinylcuprate [(CH₂=CH)₂CuLi] for the synthesis of each of the following compounds?

c.

d.

What are the products of the following reactions?

a.

b.

What vinylic halide couples with styrene (C₆H₅-CH=CH₂) in order to synthesize each of the following compounds using a Heck reaction?

c.

Using ethynylcyclohexane as a starting material and any other needed reagents, how can the following compounds be synthesized?

a.

What are the products of the following reactions?

b.

What are the products of the following reactions?

d.

Using the given starting material, any necessary inorganic reagents and catalysts, and any carbon-containing compounds with no more than two carbons, indicate how each of the following compounds can be prepared:

a.

Using the given starting material, any necessary inorganic reagents and catalysts, and any carbon-containing compounds with no more than two carbons, indicate how each of the following compounds can be prepared:

b.

Using the given starting material, any necessary inorganic reagents and catalysts, and any carbon-containing compounds with no more than two carbons, indicate how each of the following compounds can be prepared:

c.

Dimerization is a side reaction that occurs during the preparation of a Grignard reagent. Propose a mechanism that accounts for the formation of the dimer.

A student added an equivalent of 3,4-epoxy-4-methylcyclohexanol to a solution of methylmagnesium bromide in diethyl ether, and then added dilute hydrochloric acid. He expected that the product would be 1,2-dimethyl-1,4-cyclohexanediol. He did not get any of the expected product. What product did he get?

Using the given starting material, any necessary inorganic reagents, and any carbon-containing compounds with no more than two carbons, indicate how each of the following compounds can be prepared:

b.

Which of the following compounds cannot be prepared by a Heck reaction?

For those compounds that can be prepared by a Heck reaction, what starting materials are required?

Metathesis of which of the following sets of alkenes leads to the highest yield of a single alkene?

1. 1-butene and 1-pentene 

2. 2-butene and 3-hexene 

3. 2-butene and 1-pentene

A dibromide loses only one bromine when it reacts with sodium hydroxide. The dibromide forms toluene (C₆H₅-CH₃) when it reacts with magnesium shavings in ether followed by treatment with dilute acid. Give possible structures for the dibromide.

What starting material is required in order to synthesize each of the following compounds by ring-closing metathesis?

a.

What product is obtained from ring-opening metathesis polymerization of each of the following compounds? (Hint: In each case, the product is an unsaturated hydrocarbon with a high molecular weight.)

a.

a. Show the reagents required to form the primary alcohol in each of the following reactions.

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 α-bromo ester with zinc.

Describe how each of the following compounds can be prepared, using a Reformatsky reaction:

d.

What are the products of the following reactions? Show all stereoisomers that are formed.

a.

b.