10 attempts left R-C=CH Alkynes undergo hydroboration to give alkenylboranes, which can be oxidized to give carbonyl compounds with hydrogen peroxide. The net result of the two-step sequence is hydration, which gives aldehydes from terminal alkynes. Check my work 1. R₂BH 2. H₂0₂, NaOH R H H H₂O2 R H BR¹2 Alkenylborane The oxidation step involves an enol intermediate. Using the following mechanism as a guide, draw the structure of the enol that is formed in the conversion of 1-hexyne to hexanal. Click the "draw structure" button to launch the drawing utility.
10 attempts left R-C=CH Alkynes undergo hydroboration to give alkenylboranes, which can be oxidized to give carbonyl compounds with hydrogen peroxide. The net result of the two-step sequence is hydration, which gives aldehydes from terminal alkynes. Check my work 1. R₂BH 2. H₂0₂, NaOH R H H H₂O2 R H BR¹2 Alkenylborane The oxidation step involves an enol intermediate. Using the following mechanism as a guide, draw the structure of the enol that is formed in the conversion of 1-hexyne to hexanal. Click the "draw structure" button to launch the drawing utility.
Chemistry
10th Edition
ISBN:9781305957404
Author:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Publisher:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Chapter1: Chemical Foundations
Section: Chapter Questions
Problem 1RQ: Define and explain the differences between the following terms. a. law and theory b. theory and...
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Alkynes undergo hydroboration to give alkenylboranes, which can be oxidized to give carbonyl
compounds with hydrogen peroxide. The net result of the two-step sequence is hydration, which gives
aldehydes from terminal alkynes.
R-C=CH
1. R'₂BH
2. H₂O2, NaOH
Conversion of an Enol to a Ketone
THE OVERALL REACTION:
H
RCH
Enol
H
Hydronium ion
OH
R'
The oxidation step involves an enol intermediate. Using the following mechanism as a guide, draw the
structure of the enol that is formed in the conversion of 1-hexyne to hexanal. Click the "draw
structure" button to launch the drawing utility.
+RCH:
Enol
Check my work
R
R'
BR 2
Alkenylborane
OH
H
H
THE MECHANISM:
Step 1: In aqueous acid, the first step is proton transfer to the carbon-carbon
double bond.
H₂O2
Ketone
(aldehyde if R' = H)
H
`'R'
H
Water
R
1
:O:+ RCH-
+ÖH
H
R'
H
Conjugate acid
of ketone](/v2/_next/image?url=https%3A%2F%2Fcontent.bartleby.com%2Fqna-images%2Fquestion%2Fed1f285c-10df-4716-ad94-079cc9578304%2F6caa9471-23d2-41e6-92bb-f6d99292922d%2Fbn5grm8_processed.jpeg&w=3840&q=75)
Transcribed Image Text:25
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10 attempts left
Alkynes undergo hydroboration to give alkenylboranes, which can be oxidized to give carbonyl
compounds with hydrogen peroxide. The net result of the two-step sequence is hydration, which gives
aldehydes from terminal alkynes.
R-C=CH
1. R'₂BH
2. H₂O2, NaOH
Conversion of an Enol to a Ketone
THE OVERALL REACTION:
H
RCH
Enol
H
Hydronium ion
OH
R'
The oxidation step involves an enol intermediate. Using the following mechanism as a guide, draw the
structure of the enol that is formed in the conversion of 1-hexyne to hexanal. Click the "draw
structure" button to launch the drawing utility.
+RCH:
Enol
Check my work
R
R'
BR 2
Alkenylborane
OH
H
H
THE MECHANISM:
Step 1: In aqueous acid, the first step is proton transfer to the carbon-carbon
double bond.
H₂O2
Ketone
(aldehyde if R' = H)
H
`'R'
H
Water
R
1
:O:+ RCH-
+ÖH
H
R'
H
Conjugate acid
of ketone
![THE MECHANISM:
Step 1: In aqueous acid, the first step is proton transfer to the carbon-carbon
double bond.
H
BOH
H
Hydronium ion
RCH₂
R'
Conjugate acid
of ketone
1-Hexyne
draw structure...
+RCH=
SÖH
Enol
Step 2: The conjugate acid of the ketone transfers a proton from oxygen to a water
molecule, yielding a ketone.
¹H-
H
+ :0:
R'
H
Water
H
:O: +RCH-
H
Water
1. R'₂BH
2. H₂O₂, NaOH
RCH₂
Ketone
R'
R'
H
Conjugate acid
of ketone
+ÖH
+
Hexanal
H
H-O:
H
Hydronium
ion
H](/v2/_next/image?url=https%3A%2F%2Fcontent.bartleby.com%2Fqna-images%2Fquestion%2Fed1f285c-10df-4716-ad94-079cc9578304%2F6caa9471-23d2-41e6-92bb-f6d99292922d%2Fcid5vjv_processed.png&w=3840&q=75)
Transcribed Image Text:THE MECHANISM:
Step 1: In aqueous acid, the first step is proton transfer to the carbon-carbon
double bond.
H
BOH
H
Hydronium ion
RCH₂
R'
Conjugate acid
of ketone
1-Hexyne
draw structure...
+RCH=
SÖH
Enol
Step 2: The conjugate acid of the ketone transfers a proton from oxygen to a water
molecule, yielding a ketone.
¹H-
H
+ :0:
R'
H
Water
H
:O: +RCH-
H
Water
1. R'₂BH
2. H₂O₂, NaOH
RCH₂
Ketone
R'
R'
H
Conjugate acid
of ketone
+ÖH
+
Hexanal
H
H-O:
H
Hydronium
ion
H
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