Skip to main content

My Courses

AI Tools Channels Home

10. Addition Reactions

Alkyne Hydroboration

10. Addition Reactions

Alkyne Hydroboration

Guided videos.

Learn with Johnny

Go to the course

Anti-Markovnikov addition of alcohols to terminal alkynes yields aldehydes

Anti-Markovnikov addition of alcohols to terminal alkynes yields aldehydes

Johnny Betancourt

Practice this topic

Multiple Choice

Predict the major, organic product for the following reaction.

Textbook Question

Answer Problem 39 , parts a–h, using 2-butyne as the starting material instead of propyne. f. R2BH in THF followed by H2O2/HO− /H2O

Textbook Question

What reagents should be used to carry out the following syntheses?

Textbook Question

Predict the major products of the following reactions. d. trans-cyclodecene + peroxyacetic acid in acidic water e. cis-cyclodecene + mCPBA in CH2Cl2, then dilute aqueous acid

Textbook Question

For each compound, give the product(s) expected from (1) HgSO4/H2SO4 - catalyzed hydration and (2) hydroboration–oxidation. d. cyclodecyne

Textbook Question

For each compound, give the product(s) expected from (1) HgSO4/H2SO4 - catalyzed hydration and (2) hydroboration–oxidation. c. hex-3-yne

Textbook Question

For each compound, give the product(s) expected from (1) HgSO4/H2SO4 - catalyzed hydration and (2) hydroboration–oxidation. b. hex-2-yne

Textbook Question

For each compound, give the product(s) expected from (1) HgSO4/H2SO4 - catalyzed hydration and (2) hydroboration–oxidation. a. hex-1-yne

Textbook Question

The hydroboration–oxidation of internal alkynes produces ketones. b. When hydroboration–oxidation is applied to pent-2-yne, two products are obtained. Show why a mixture of products should be expected with any unsymmetrical internal alkyne.

Textbook Question

The hydroboration–oxidation of internal alkynes produces ketones. a. When hydroboration–oxidation is applied to but-2-yne, a single pure product is obtained. Determine the structure of this product, and show the intermediates in its formation.

Textbook Question

Show how you would accomplish the following synthetic transformations. Show all intermediates. (j) < of reaction>

Textbook Question

Predict the products of reaction of pent-1-yne with the following reagents. (j) NaNH2 (k) H2SO4/HgSO4, H2O (l) Sia2BH, then H2O2, -OH

Textbook Question

Draw the ketone(s) you would expect to form by treating the following alkynes under the conditions of hydroboration–oxidation: (a) 6-methyloct-1-yne, (b) 1,10-dicyclohexyldec-5-yne, and (c) 5-phenylhex-2-yne. 1. BH₃ alkyne ----------------------------------> ketone 2. NaOH, H₂O₂

Textbook Question

(••) For the alkynes shows here, show the product(s) expected to form when treated under the following conditions: (vii) 1. BH₃ 2. H₂O₂, NaOH. If you expect two products, show both. (c)

Textbook Question

Predict the product of the following aldehyde/ketone syntheses. (c)

Textbook Question

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

a. <IMAGE>

Textbook Question

What are products of the following reactions?

e. <IMAGE>

Textbook Question

The following functional-group interchange is

a useful synthesis of aldehydes.

<IMAGE of reaction>

(a) What reagents were used in this chapter for

this transformation? Give an example to illustrate this method.

(b) This functional-group interchange can also be accomplished

using the following sequence.

<IMAGE of reaction>

Propose mechanisms for these steps.

Textbook Question

For each of the following alkynes, draw the products obtained from (1) the acid-catalyzed addition of water (mercuric ion is added for part a) and from (2) hydroboration–oxidation:

a. 1-butyne

Textbook Question

What is the major product of the reaction of 1 mol of propyne with each of the following reagents?

e. aqueous H2SO4, HgSO4

f. R2BH in THF followed by H2O2/HO− /H2O

Textbook Question

Explain why a single pure product is obtained from hydroboration–oxidation of 2-butyne, whereas two products are obtained from hydroboration–oxidation of 2-pentyne.

Name two other internal alkynes that yield only one product upon hydroboration–oxidation.

Textbook Question

What are products of the following reactions?

d. <IMAGE>

Textbook Question

What hydrocarbon would you use to prepare the organoboron compound in Problem 14?

<IMAGE>

Showing 23 of 23 practice