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
Organic Chemistry
- The aim of the lab is to measure the sodium content from tomato sauce using the Mohr titration method. There are two groups being: Regular Tomato sauce & Salt Reduced tomato sauce QUESTION: State how you would prepare both Regular & Salt reduced tomato sauce samples for chemical analysis using the Mohr titration methodarrow_forwardUsing the conditions of spontaneity to deduce the signs of AH and AS Use the observations about each chemical reaction in the table below to decide the sign (positive or negative) of the reaction enthalpy AH and reaction entropy AS. Note: if you have not been given enough information to decide a sign, select the "unknown" option. reaction observations conclusions A The reverse of this reaction is always spontaneous but proceeds faster at temperatures above -48. °C. ΔΗ is (pick one) ✓ AS is (pick one) B This reaction is spontaneous except below 114. °C but proceeds at a slower rate below 135. °C. ΔΗ is (pick one) AS is (pick one) ΔΗ is C This reaction is exothermic and proceeds faster at temperatures above -43. °C. (pick one) AS is (pick one) v Х 5 ? 18 Ararrow_forwardion. A student proposes the following Lewis structure for the perchlorate (CIO) io : :0: : Cl : - - : :0: ك Assign a formal charge to each atom in the student's Lewis structure. atom central O formal charge ☐ top O ☐ right O ☐ bottom O ☐ Cl ☐arrow_forward
- Decide whether these proposed Lewis structures are reasonable. proposed Lewis structure Yes. Is the proposed Lewis structure reasonable? Cl- : 2: :Z: :Z: N—N : 0: C C1: O CO No, it has the wrong number of valence electrons. The correct number is: ☐ No, it has the right number of valence electrons but doesn't satisfy the octet rule. The symbols of the problem atoms are:* ☐ Yes. No, it has the wrong number of valence electrons. The correct number is: ☐ No, it has the right number of valence electrons but doesn't satisfy the octet rule. The symbols of the problem atoms are:* | Yes. No, it has the wrong number of valence electrons. The correct number is: No, it has the right number of valence electrons but doesn't satisfy the octet rule. The symbols of the problem atoms are:* | If two or more atoms of the same element don't satisfy the octet rule, just enter the chemical symbol as many times as necessary. For example, if two oxygen atoms don't satisfy the octet rule, enter "0,0". ☑arrow_forwardUse the observations about each chemical reaction in the table below to decide the sign (positive or negative) of the reaction enthalpy AH and reaction entropy AS. Note: if you have not been given enough information to decide a sign, select the "unknown" option. reaction observations conclusions ΔΗ is (pick one) A This reaction is faster above 103. °C than below. AS is (pick one) ΔΗ is (pick one) B This reaction is spontaneous only above -9. °C. AS is (pick one) ΔΗ is (pick one) C The reverse of this reaction is always spontaneous. AS is (pick one) 18 Ararrow_forwardUse the observations about each chemical reaction in the table below to decide the sign (positive or negative) of the reaction enthalpy AH and reaction entropy AS. Note: if you have not been given enough information to decide a sign, select the "unknown" option. reaction observations conclusions A The reverse of this reaction is always spontaneous but proceeds slower at temperatures below 41. °C. ΔΗ is (pick one) AS is (pick one) ΔΗ is (pick one) B This reaction is spontaneous except above 94. °C. AS is (pick one) This reaction is always spontaneous, but ΔΗ is (pick one) C proceeds slower at temperatures below −14. °C. AS is (pick one) Х 00. 18 Ar 무ㅎ B 1 1arrow_forward
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- (2 pts) Why is O2 more stable as a diatomic molecule than S2?arrow_forwardDraw the Lewis structure for the polyatomic phosphite (PO¾³¯) a anion. Be sure to include all resonance structures that satisfy the octet rule. C I A [ ]¯arrow_forwardDecide whether these proposed Lewis structures are reasonable. proposed Lewis structure Is the proposed Lewis structure reasonable? Yes. :0: Cl C C1: 0=0: : 0 : : 0 : H C N No, it has the wrong number of valence electrons. The correct number is: ☐ No, it has the right number of valence electrons but doesn't satisfy the octet rule. The symbols of the problem atoms are:* ☐ Yes. No, it has the wrong number of valence electrons. The correct number is: ☐ No, it has the right number of valence electrons but doesn't satisfy the octet rule. The symbols of the problem atoms are:* Yes. ☐ No, it has the wrong number of valence electrons. The correct number is: ☐ No, it has the right number of valence electrons but doesn't satisfy the octet rule. The symbols of the problem atoms are:* | * If two or more atoms of the same element don't satisfy the octet rule, just enter the chemical symbol as many times as necessary. For example, if two oxygen atoms don't satisfy the octet rule, enter "0,0".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