a)
Interpretation:
The product of the Wolff-Kishner reduction reaction shown is to be given. The electron-pushing mechanism, beginning from the hydrazone intermediate is to be provided.
Concept introduction:
In Wolff-Kishner reduction
To give:
The product of the Wolff-Kishner reduction reaction shown.
To provide:
The electron-pushing mechanism, beginning from the hydrazone intermediate.
Answer to Problem 38MP
The product of the Wolff-Kishner reduction reaction shown is
The electron-pushing mechanism for the formation of the alkane, beginning from the hydrazone intermediate, is given below.
Explanation of Solution
The hydroxide ion from KOH abstracts a weakly acidic H from –NH2 of the hydrazone of isopropyl phenyl ketone to yield a carbanion which picks up a proton to yield a neutral intermediate. Deprotonation of the remaining hydrogen on N by the hydroxide ion occurs with the eliminartion of nitrogen to yield another carbanion which is protonated to give the alkane, ethyl benzene, as the product.
The product of the Wolff-Kishner reduction reaction shown is
The electron-pushing mechanism, beginning from the hydrazone intermediate is given below.
b)
Interpretation:
The product of the Wolff-Kishner reduction reaction shown is to be given. The electron-pushing mechanism, beginning from the hydrazone intermediate is to be provided.
Concept introduction:
In Wolff-Kishner reduction aldehydes and ketones react with hydrazine in the presence of a base to yield alkanes. First a hydrazone is formed which is then converted into an alkane.
To give:
The product of the Wolff-Kishner reduction reaction shown.
To provide:
The electron-pushing mechanism the formation of the alkane beginning from the hydrazone intermediate.
Answer to Problem 38MP
The product of the Wolff-Kishner reduction reaction shown is
The electron-pushing mechanism the formation of the alkane, beginning from the hydrazone intermediate, is given below.
Explanation of Solution
The hydroxide ion from KOH abstracts a weakly acidic H from –NH2 of the hydrazone of diethyl ketone to yield a carbanion which picks up a proton to yield a neutral intermediate. Deprotonation of the remaining hydrogen on N by the hydroxide ion occurs with the eliminartion of nitrogen to yield another carbanion which is protonated to give the alkane, n-pentane, as the product.
The product of the Wolff-Kishner reduction reaction shown is
The electron-pushing mechanism, beginning from the hydrazone intermediate is given below.
c)
Interpretation:
The product of the Wolff-Kishner reduction reaction shown is to be given. The electron-pushing mechanism, beginning from the hydrazone intermediate is to be provided.
Concept introduction:
In Wolff-Kishner reduction aldehydes and ketones react with hydrazine in the presence of a base to yield alkanes. First a hydrazone is formed which is then converted into an alkane.
To give:
The product of the Wolff-Kishner reduction reaction shown.
To provide:
The electron-pushing mechanism the formation of the alkane beginning from the hydrazone intermediate.
Answer to Problem 38MP
The product of the Wolff-Kishner reduction reaction shown is
The electron-pushing mechanism the formation of the alkane, beginning from the hydrazone intermediate, is given below.
Explanation of Solution
The hydroxide ion from KOH abstracts a weakly acidic H from –NH2 of the hydrazone of the ketone to yield a carbanion which picks up a proton to yield a neutral intermediate. Deprotonation of the remaining hydrogen on N by the hydroxide ion occurs with the eliminartion of nitrogen to yield another carbanion which is protonated to give the alkane as the product.
The product of the Wolff-Kishner reduction reaction shown is
The electron-pushing mechanism, beginning from the hydrazone intermediate is given below.
d)
Interpretation:
The product of the Wolff-Kishner reduction reaction shown is to be given. The electron-pushing mechanism, beginning from the hydrazone intermediate is to be provided.
Concept introduction:
In Wolff-Kishner reduction aldehydes and ketones react with hydrazine in the presence of a base to yield alkanes. First a hydrazone is formed which is then converted into an alkane.
To give:
The product of the Wolff-Kishner reduction reaction shown.
To provide:
The electron-pushing mechanism, beginning from the hydrazone intermediate.
Answer to Problem 38MP
The product of the Wolff-Kishner reduction reaction shown is
The electron-pushing mechanism for the formation of the alkane beginning from the hydrazone intermediate, is given below.
Explanation of Solution
The hydroxide ion from KOH abstracts a weakly acidic H from –NH2 of the hydrazone of ketone to yield a carbanion which picks up a proton to yield a neutral intermediate. Deprotonation of the remaining hydrogen on N by the hydroxide ion occurs with the eliminartion of nitrogen to yield another carbanion which is protonated to give the alkane as the product.
The product of the Wolff-Kishner reduction reaction shown is
The electron-pushing mechanism for the formation of the alkane beginning from the hydrazone intermediate, is given below.
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Chapter 19 Solutions
EBK ORGANIC CHEMISTRY
- Predicting As the lead product manager at OrganometALEKS Industries, you are trying to decide if the following reaction will make a molecule with a new C - C bond as its major product: H₂N O H 1. ? 2. H3O+ If this reaction will work, draw the major organic product or products you would expect in the drawing area below. If there's more than one major product, you can draw them in any arrangement you like. Be sure you use wedge and dash bonds if necessary, for example to distinguish between major products with different stereochemistry. 0 If the major products of this reaction won't have a new CC bond, just check the box under the drawing area and leave it blank. فا Explanation Check Click and drag to start drawing a structure.arrow_forwardHighlight the chirality (or stereogenic) center(s) in the given compound. A compound may have one or more stereogenic centers. OH OH OH OH OH OHarrow_forwardUsing wedge-and-dash bonds, modify the bonds on the chiral carbon in the molecule below so the molecule has R stereochemical configuration. NH H Br X टेarrow_forward
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- Please draw the structure in the box that is consistent with all the spectral data and alphabetically label all of the equivalent protons in the structure (Ha, Hb, Hc....) in order to assign all the proton NMR peaks. The integrations are computer generated and approximate the number of equivalent protons. Molecular formula: C13H1802 14 13 12 11 10 11 (ppm) Structure with assigned H peaks 2.08 3.13arrow_forwardCHEMICAL KINETICS. One of the approximation methods for solving the rate equation is the steady-state approximation method. Explain what it consists of.arrow_forwardCHEMICAL KINETICS. One of the approximation methods for solving the rate equation is the limiting or determining step approximation method. Explain what it consists of.arrow_forward
Organic ChemistryChemistryISBN:9781305580350Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. FootePublisher:Cengage Learning
EBK A SMALL SCALE APPROACH TO ORGANIC LChemistryISBN:9781305446021Author:LampmanPublisher:CENGAGE LEARNING - CONSIGNMENT