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14. Synthetic Techniques

Alkynide Alkylation

14. Synthetic Techniques

Alkynide Alkylation

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Sodium Alkynide Alkylation

Sodium Alkynide Alkylation

Johnny Betancourt

Practice this topic

Multiple Choice

Propose a synthesis:

Multiple Choice

Propose a synthesis:

Multiple Choice

Multiple Choice

Which of the following syntheses will best produce the following target molecule?

Textbook Question

Show how you would accomplish the following syntheses.

You may use whatever additional reagents you need.

(f) <IMAGE of reaction>

Textbook Question

Show how you would accomplish the following synthetic

conversions. You may use any additional reagents

and solvents you need.

(d) <IMAGE of reaction>

Textbook Question

a. Show how the following compounds can be prepared, using ethyne as one of the starting materials:

2. 1-phenyl-2-butyn-1-ol

Textbook Question

Show how you would synthesize the following compounds, starting with acetylene and any compounds containing no more than four carbon atoms. (g) pentanal, CH3CH2CH2CH2CHO (h) pentan-2-one, CH3-CO-CH2CH2CH3 (i) (±) 3,4-dibromohexane

Textbook Question

How can the following compounds be prepared using ethyne as the starting material?

c. <IMAGE>

Textbook Question

Show how each of the following compounds can be synthesized from the given starting materials:

b. <IMAGE>

Textbook Question

(••) Suggest a method for synthesizing the following alkynes using an alkyne and an alkyl halide. [There are two correct answers for each product.]

(c) <IMAGE>

Textbook Question

When doing synthesis, you will often find yourself repeating the same series of steps. To see this in action, synthesize the following aldehydes beginning with an organic molecule containing three carbons or fewer.

(d) <IMAGE>

Textbook Question

Show how each of the following compounds can be prepared using the given starting material, any needed inorganic reagents, and any organic compound that has no more than four carbons:

b. <IMAGE>

Textbook Question

Show how each of the following compounds can be synthesized from the given starting materials:

d. <IMAGE>

Textbook Question

Predict the products formed when <IMAGE> reacts with the following compounds.

(d) cyclohexanone

(e) CH₃CH₂CH₂CHO

Textbook Question

The application box in the margin of page 437 states,

“The addition of an acetylide ion to a carbonyl group is used

in the synthesis of ethchlorvynol, a drug used to cause

drowsiness and induce sleep.”

Show how you would accomplish this synthesis

from acetylene and a carbonyl compound.

<IMAGE>

Textbook Question

a. Show how the following compounds can be prepared, using ethyne as one of the starting materials: 1. 1-pentyn-3-ol

Textbook Question

How could the following compounds be synthesized from acetylene? b.

Textbook Question

Reaction of the acetylide with the epoxide shown will not form the desired product. What side reaction occurs instead? Why?

Textbook Question

Beginning with the molecules on the left of each chemical equation, synthesize the molecules shown. While there can be multiple ways of doing each synthesis, the minimum number of steps necessary is indicated over each reaction arrow. (b)

Textbook Question

(•••) Beginning with the molecules on the left, provide a synthesis of the molecule on the right. The ideal number of steps is indicated over the reaction arrow, although there may be alternate routes worth considering. (b)

Textbook Question

(•••) Synthesize the following molecules beginning with only organic molecules containing three carbons or fewer. (b)

Textbook Question

(•••) Synthesize the following molecules beginning with only organic molecules containing three carbons or fewer. (e)

Textbook Question

For each of the following target molecules, design a multistep synthesis to show how it can be prepared from the given starting material: c.

Textbook Question

Show how each of the following compounds can be synthesized from the given starting materials: c.

Textbook Question

Show how each of the following compounds can be prepared using the given starting material, any needed inorganic reagents, and any organic compound that has no more than four carbons: a.

Textbook Question

Show how each of the following compounds can be prepared using the given starting material, any needed inorganic reagents, and any organic compound that has no more than four carbons: c.

Textbook Question

Show how the following compound can be prepared from the given starting material. Draw the structure of the compound that is formed in each step of the synthesis.

Textbook Question

Show how you would synthesize each compound, beginning with acetylene and any necessary additional reagents a. prop-2-yn-1-ol (propargyl alcohol) H—C≡C—CH2OH

Textbook Question

Show how you would synthesize each compound, beginning with acetylene and any necessary additional reagents b. hept-2-yn-4-ol

Textbook Question

Show how you would synthesize 2-phenylhex-3-yn-2-ol, starting with acetophenone (PhCOCH3) and any other reagents you need. ('2-ol' means there is an OH group on C2.)

Textbook Question

(••) Complete the following synthesis by providing the necessary reagents.

<IMAGE>

Textbook Question

Beginning with the molecules on the left of each chemical equation, synthesize the molecules shown. While there can be multiple ways of doing each synthesis, the minimum number of steps necessary is indicated over each reaction arrow.

(c) <IMAGE>

(Hint: H₂C = O is also made in this reaction.)

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