10. Addition Reactions
Alkyne Hydroboration
10. Addition Reactions
Alkyne Hydroboration - Video Tutorials & Practice Problems
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Get a 10 bullets summary of the topicHydroboration-oxidation of terminal alkynes leads to formation of aldehydes. (If the alkyne is not terminal, it will just yield a ketone).Â
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Anti-Markovnikov addition of alcohols to terminal alkynes yields aldehydes
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This reaction yields an anti-Markovnikov vinyl alcohol, which will tautomerize into a carbonyl on the terminal position, which is the definition of an aldehyde.
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PRACTICE PROBLEMS AND ACTIVITIES (87)
- d. Is the reaction of 1-butene with HBr regioselective? e. Is it stereoselective? f. Is it stereospecific?
- Which electrophilic addition reactions d. form a five-membered ring intermediate?
- Which electrophilic addition reactions c. form a three-membered ring
- Which electrophilic addition reactions a. form a carbocation intermediate? intermediate?
- What characteristics must the reactant of a stereospecific reaction have?
- Draw the products of the following reactions, including their configurations:
- What reagents are needed to carry out the following syntheses?
- What reagents are needed to carry out the following syntheses?
- What reagents are needed to carry out the following syntheses?
- Draw the products of the following reactions, including their configurations:
- Draw the products of the following reactions, including their configurations:
- A, a compound with molecular formula C6H10, contains three methylene units. A reacts with one equivalent of H2...
- What reagents are needed to carry out the following syntheses?
- Explain why, in hydroboration–oxidation, HO− and HOOH cannot be added until after the hydroboration reaction i...
- Answer Problem 39 , parts a–h, using 2-butyne as the starting material instead of propyne. f. R2BH in THF fol...
- Answer Problem 39 , parts a–h, using 2-butyne as the starting material instead of propyne. e. aqueous H2SO4, ...
- a. Starting with 3-methyl-1-butyne, how can you prepare the following alcohols? 2. 3-methyl-1-butanol b. In ...
- What reagents should be used to carry out the following syntheses?
- What reagents should be used to carry out the following syntheses?
- Show how the following compound can be prepared from the given starting material. Draw the structure of the co...
- Show how each of the following compounds can be prepared using the given starting material, any needed inorgan...
- Show how each of the following compounds can be prepared using the given starting material, any needed inorgan...
- Show how the following compounds can be synthesized starting with ethyne: a. cis-2-octene
- How can the following compounds be synthesized, starting with a hydrocarbon that has the same number of carbon...
- Show how you would synthesize each compound, starting with alkenes or cycloalkenes that contain no more than s...
- Complete each synthesis by providing the structure of the major product at each step, including any important ...
- Complete each synthesis by providing the structure of the major product at each step, including any important ...
- Predict the major products of the following reactions, and give the structures of any intermediates. Include s...
- Show how you would accomplish the following conversions. c. trans-hex-3-ene to meso-hexane-3,4-diol
- Show how you would accomplish the following conversions. b. cis-hex-3-ene to (d,l)-hexane-3,4-diol
- Predict the major products of the following reactions. d. trans-cyclodecene + peroxyacetic acid in acidic wat...
- Predict the major products of the following reactions. b. trans-hex-3-ene + peroxyacetic acid (CH3CO3H) in wa...
- Show how you would synthesize each compound, starting with alkenes or cycloalkenes that contain no more than s...
- Show how you would accomplish each of the following synthetic conversions. c. cyclohexanol-->
- Show how you would accomplish the following transformations. c. 1-methylcycloheptanol-->2-methylcyclohepta...
- Show how you would accomplish the following synthetic conversions. c. 2-bromo-2,4-dimethylpentane -> 2,4-d...
- Propose a mechanism for the following reaction. .
- In contact with a platinum catalyst, an unknown alkene reacts with three equivalents of hydrogen gas to give 1...
- For each compound, give the product(s) expected from (1) HgSO4/H2SO4 - catalyzed hydration and (2) hydroborati...
- For each compound, give the product(s) expected from (1) HgSO4/H2SO4 - catalyzed hydration and (2) hydroborati...
- For each compound, give the product(s) expected from (1) HgSO4/H2SO4 - catalyzed hydration and (2) hydroborati...
- For each compound, give the product(s) expected from (1) HgSO4/H2SO4 - catalyzed hydration and (2) hydroborati...
- The hydroboration–oxidation of internal alkynes produces ketones. b. When hydroboration–oxidation is applied ...
- The hydroboration–oxidation of internal alkynes produces ketones. a. When hydroboration–oxidation is applied ...
- Show how you would accomplish the following synthetic transformations. Show all intermediates. (j) < of re...
- Show how you would accomplish the following synthetic transformations. Show all intermediates. (i) < of re...
- Show how you would accomplish the following synthetic transformations. Show all intermediates. (f) < of re...
- Show how you would accomplish the following synthetic transformations. Show all intermediates. (e) < of re...
- Show how you would accomplish the following synthetic transformations. Show all intermediates. (d) < of re...
- Show how you would accomplish the following synthetic transformations. Show all intermediates. (c) < of re...
- Show how you would accomplish the following synthetic transformations. Show all intermediates. (b) < of re...
- Show how you would accomplish the following synthetic transformations. Show all intermediates. (a) < of re...
- Using hex-1-ene as your starting material, show how you would synthesize the following compounds. (Once you ...
- Using hex-1-ene as your starting material, show how you would synthesize the following compounds. (Once you ...
- Show how hex-1-yne might be converted to a. 1,2-dichlorohex-1-ene. b. 1-bromohex-1-ene. c. 2-bromohex-1-ene...
- Predict the products of reaction of pent-1-yne with the following reagents. (j) NaNH2 (k) H2SO4/HgSO4, H2O (l...
- Predict the products of reaction of pent-1-yne with the following reagents. (g) cold, dilute KMnO4 (h) warm, ...
- Predict the products of reaction of pent-1-yne with the following reagents. (d) H2, Pd/BaSO4, quinoline (e) 1...
- Predict the products of reaction of pent-1-yne with the following reagents. (a) 1 equivalent of HCl (b) 2 equ...
- When treated with hydrogen and a platinum catalyst, an unknown compound X absorbs 5 equivalents of hydrogen ...
- Show how each of the following compounds can be synthesized from the given starting materials: c.
- Starting with cyclohexene, how can the following compounds be prepared? c. dicyclohexyl ether
- Starting with cyclohexene, how can the following compounds be prepared? b. cyclohexylmethylamine
- For each of the following target molecules, design a multistep synthesis to show how it can be prepared from t...
- For each of the following target molecules, design a multistep synthesis to show how it can be prepared from t...
- (•••) Retrosynthetic analysis is the process of working backward to develop the synthesis of a new compound. I...
- (•••) Retrosynthetic analysis is the process of working backward to develop the synthesis of a new compound. I...
- (•••) Retrosynthetic analysis is the process of working backward to develop the synthesis of a new compound. I...
- Show how you would accomplish the following synthetic transformations. Show all intermediates. (g) < of re...
- Write the appropriate reagent over each arrow.
- Fill in each box with the appropriate reagent: c.
- Fill in each box with the appropriate reagent: b.
- Fill in each box with the appropriate reagent: a.
- Draw the ketone(s) you would expect to form by treating the following alkynes under the conditions of hydrobor...
- For each of the following ketones/aldehydes, indicate whether it is possible to synthesize it from an alkyne a...
- (••) For the alkynes shows here, show the product(s) expected to form when treated under the following conditi...
- When doing synthesis, you will often find yourself repeating the same series of steps. To see this in action, ...
- Beginning with the molecules on the left of each chemical equation, synthesize the molecules shown. While ther...
- (••) Suggest a method for synthesizing the following alkynes using an alkyne and an alkyl halide. [There are t...
- (•••) Beginning with the molecules on the left, provide a synthesis of the molecule on the right. The ideal nu...
- (•••) Synthesize the following molecules beginning with only organic molecules containing three carbons or few...
- (•••) Synthesize the following molecules beginning with only organic molecules containing three carbons or few...
- (•••) When alkynes are treated with water and bromine a bromoketone is produced. Provide a plausible arrow-pus...
- Predict the products of the following reactions. (j) (k) (l)
- b. What would the yield be if two more steps (each with an 80% yield) were added to the synthesis?
- Predict the product of the following aldehyde/ketone syntheses. (c)
- Beginning with acetylene and benzyl bromide and using any other inorganic reagents, propose a synthesis of the...