Similarities between the mechanism of deamination of β- aminoalcohol using nitrous acid and Pinacol rearrangement has to be given. Concept Introduction: Tiffeneau–Demjanov reaction: It is an organic reaction where 1-aminomethyl-cycloalkanol gets converted to an enlarged cycloketone by reacting with nitrous acid. Pinacol rearrangement: For all glycols Pinacol rearrangement occurs. Unsymmetrical vicinal diols reveal that –OH group that becomes protonated and leaves in the one that gives rise to more stable carbocation. Acid-catalyzed conversion of Pinacol to pinacolone followed by four step mechanism as follows, Step 1: Add proton (protonation of Pinacol using acid catalyst). Step 2: Break a bond to give a stable molecules or ions (formation of carbocation). Step 3: 1, 2-shift (migration of substituent from α- to β- carbon). Step 4: deprotonation occurs (take a proton away).

Question

1) a) Give the dominant Intermolecular Force (IMF) in a sample of each of the following compounds. Please show your work. (8) SF2, CH,OH, C₂H₂ b) Based on your answers given above, list the compounds in order of their Boiling Point from low to high. (8)

Answer 1

Question

Chapter 23, Problem 23.37P

(a)

Interpretation Introduction

Interpretation:

Similarities between the mechanism of deamination of β- aminoalcohol using nitrous acid and Pinacol rearrangement has to be given.

Concept Introduction:

Tiffeneau–Demjanov reaction: It is an organic reaction where 1-aminomethyl-cycloalkanol gets converted to an enlarged cycloketone by reacting with nitrous acid.

Pinacol rearrangement: For all glycols Pinacol rearrangement occurs. Unsymmetrical vicinal diols reveal that –OH group that becomes protonated and leaves in the one that gives rise to more stable carbocation. Acid-catalyzed conversion of Pinacol to pinacolone followed by four step mechanism as follows,

Step 1: Add proton (protonation of Pinacol using acid catalyst).

Step 2: Break a bond to give a stable molecules or ions (formation of carbocation).

Step 3: 1, 2-shift (migration of substituent from α- to β- carbon).

Step 4: deprotonation occurs (take a proton away).

(b)

Interpretation Introduction

Interpretation:

Reason for the expansion of ring in the deamination of β- aminoalcohol using nitrous acid not in Pinacol rearrangement has to be explained.

Concept Introduction:

Tiffeneau–Demjanov reaction: It is an organic reaction where 1-aminomethyl-cycloalkanol gets converted to an enlarged cycloketone by reacting with nitrous acid.

Pinacol rearrangement: For all glycols Pinacol rearrangement occurs. Unsymmetrical vicinal diols reveal that –OH group that becomes protonated and leaves in the one that gives rise to more stable carbocation. Acid-catalyzed conversion of Pinacol to pinacolone followed by four step mechanism as follows,

Step 1: Add proton (protonation of Pinacol using acid catalyst).

Step 2: Break a bond to give a stable molecules or ions (formation of carbocation).

Step 3: 1, 2-shift (migration of substituent from α- to β- carbon).

Step 4: deprotonation occurs (take a proton away).

(b)

Interpretation Introduction

Interpretation:

β- Aminoalcohol that gives cyclohexanecarbaldehyde has to be suggested.

Concept Introduction:

Tiffeneau–Demjanov reaction: It is an organic reaction where 1-aminomethyl-cycloalkanol gets converted to an enlarged cycloketone by reacting with nitrous acid.

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1) a) Give the dominant Intermolecular Force (IMF) in a sample of each of the following compounds. Please show your work. (8) SF2, CH,OH, C₂H₂ b) Based on your answers given above, list the compounds in order of their Boiling Point from low to high. (8)

19.78 Write the products of the following sequences of reactions. Refer to your reaction road- maps to see how the combined reactions allow you to "navigate" between the different functional groups. Note that you will need your old Chapters 6-11 and Chapters 15-18 roadmaps along with your new Chapter 19 roadmap for these. (a) 1. BHS 2. H₂O₂ 3. H₂CrO4 4. SOCI₂ (b) 1. Cl₂/hv 2. KOLBU 3. H₂O, catalytic H₂SO4 4. H₂CrO4 Reaction Roadmap An alkene 5. EtOH 6.0.5 Equiv. NaOEt/EtOH 7. Mild H₂O An alkane 1.0 2. (CH3)₂S 3. H₂CrO (d) (c) 4. Excess EtOH, catalytic H₂SO OH 4. Mild H₂O* 5.0.5 Equiv. NaOEt/EtOH An alkene 6. Mild H₂O* A carboxylic acid 7. Mild H₂O* 1. SOC₁₂ 2. EtOH 3.0.5 Equiv. NaOEt/E:OH 5.1.0 Equiv. NaOEt 6. NH₂ (e) 1. 0.5 Equiv. NaOEt/EtOH 2. Mild H₂O* Br (f) i H An aldehyde 1. Catalytic NaOE/EtOH 2. H₂O*, heat 3. (CH,CH₂)₂Culi 4. Mild H₂O* 5.1.0 Equiv. LDA Br An ester 4. NaOH, H₂O 5. Mild H₂O* 6. Heat 7. MgBr 8. Mild H₂O* 7. Mild H₂O+

Li+ is a hard acid. With this in mind, which if the following compounds should be most soluble in water? Group of answer choices LiBr LiI LiF LiCl

Answer 2

Question

Chapter 23, Problem 23.37P

(a)

Interpretation Introduction

Interpretation:

Similarities between the mechanism of deamination of β- aminoalcohol using nitrous acid and Pinacol rearrangement has to be given.

Concept Introduction:

Tiffeneau–Demjanov reaction: It is an organic reaction where 1-aminomethyl-cycloalkanol gets converted to an enlarged cycloketone by reacting with nitrous acid.

Pinacol rearrangement: For all glycols Pinacol rearrangement occurs. Unsymmetrical vicinal diols reveal that –OH group that becomes protonated and leaves in the one that gives rise to more stable carbocation. Acid-catalyzed conversion of Pinacol to pinacolone followed by four step mechanism as follows,

Step 1: Add proton (protonation of Pinacol using acid catalyst).

Step 2: Break a bond to give a stable molecules or ions (formation of carbocation).

Step 3: 1, 2-shift (migration of substituent from α- to β- carbon).

Step 4: deprotonation occurs (take a proton away).

(b)

Interpretation Introduction

Interpretation:

Reason for the expansion of ring in the deamination of β- aminoalcohol using nitrous acid not in Pinacol rearrangement has to be explained.

Concept Introduction:

Tiffeneau–Demjanov reaction: It is an organic reaction where 1-aminomethyl-cycloalkanol gets converted to an enlarged cycloketone by reacting with nitrous acid.

Pinacol rearrangement: For all glycols Pinacol rearrangement occurs. Unsymmetrical vicinal diols reveal that –OH group that becomes protonated and leaves in the one that gives rise to more stable carbocation. Acid-catalyzed conversion of Pinacol to pinacolone followed by four step mechanism as follows,

Step 1: Add proton (protonation of Pinacol using acid catalyst).

Step 2: Break a bond to give a stable molecules or ions (formation of carbocation).

Step 3: 1, 2-shift (migration of substituent from α- to β- carbon).

Step 4: deprotonation occurs (take a proton away).

(b)

Interpretation Introduction

Interpretation:

β- Aminoalcohol that gives cyclohexanecarbaldehyde has to be suggested.

Concept Introduction:

Tiffeneau–Demjanov reaction: It is an organic reaction where 1-aminomethyl-cycloalkanol gets converted to an enlarged cycloketone by reacting with nitrous acid.

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Answer 3

Question

Chapter 23, Problem 23.37P

(a)

Interpretation Introduction

Interpretation:

Similarities between the mechanism of deamination of β- aminoalcohol using nitrous acid and Pinacol rearrangement has to be given.

Concept Introduction:

Tiffeneau–Demjanov reaction: It is an organic reaction where 1-aminomethyl-cycloalkanol gets converted to an enlarged cycloketone by reacting with nitrous acid.

Pinacol rearrangement: For all glycols Pinacol rearrangement occurs. Unsymmetrical vicinal diols reveal that –OH group that becomes protonated and leaves in the one that gives rise to more stable carbocation. Acid-catalyzed conversion of Pinacol to pinacolone followed by four step mechanism as follows,

Step 1: Add proton (protonation of Pinacol using acid catalyst).

Step 2: Break a bond to give a stable molecules or ions (formation of carbocation).

Step 3: 1, 2-shift (migration of substituent from α- to β- carbon).

Step 4: deprotonation occurs (take a proton away).

(b)

Interpretation Introduction

Interpretation:

Reason for the expansion of ring in the deamination of β- aminoalcohol using nitrous acid not in Pinacol rearrangement has to be explained.

Concept Introduction:

Tiffeneau–Demjanov reaction: It is an organic reaction where 1-aminomethyl-cycloalkanol gets converted to an enlarged cycloketone by reacting with nitrous acid.

Pinacol rearrangement: For all glycols Pinacol rearrangement occurs. Unsymmetrical vicinal diols reveal that –OH group that becomes protonated and leaves in the one that gives rise to more stable carbocation. Acid-catalyzed conversion of Pinacol to pinacolone followed by four step mechanism as follows,

Step 1: Add proton (protonation of Pinacol using acid catalyst).

Step 2: Break a bond to give a stable molecules or ions (formation of carbocation).

Step 3: 1, 2-shift (migration of substituent from α- to β- carbon).

Step 4: deprotonation occurs (take a proton away).

(b)

Interpretation Introduction

Interpretation:

β- Aminoalcohol that gives cyclohexanecarbaldehyde has to be suggested.

Concept Introduction:

Tiffeneau–Demjanov reaction: It is an organic reaction where 1-aminomethyl-cycloalkanol gets converted to an enlarged cycloketone by reacting with nitrous acid.

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Answer 4

Question

Chapter 23, Problem 23.37P

(a)

Interpretation Introduction

Interpretation:

Similarities between the mechanism of deamination of β- aminoalcohol using nitrous acid and Pinacol rearrangement has to be given.

Concept Introduction:

Tiffeneau–Demjanov reaction: It is an organic reaction where 1-aminomethyl-cycloalkanol gets converted to an enlarged cycloketone by reacting with nitrous acid.

Pinacol rearrangement: For all glycols Pinacol rearrangement occurs. Unsymmetrical vicinal diols reveal that –OH group that becomes protonated and leaves in the one that gives rise to more stable carbocation. Acid-catalyzed conversion of Pinacol to pinacolone followed by four step mechanism as follows,

Step 1: Add proton (protonation of Pinacol using acid catalyst).

Step 2: Break a bond to give a stable molecules or ions (formation of carbocation).

Step 3: 1, 2-shift (migration of substituent from α- to β- carbon).

Step 4: deprotonation occurs (take a proton away).

(b)

Interpretation Introduction

Interpretation:

Reason for the expansion of ring in the deamination of β- aminoalcohol using nitrous acid not in Pinacol rearrangement has to be explained.

Concept Introduction:

Tiffeneau–Demjanov reaction: It is an organic reaction where 1-aminomethyl-cycloalkanol gets converted to an enlarged cycloketone by reacting with nitrous acid.

Pinacol rearrangement: For all glycols Pinacol rearrangement occurs. Unsymmetrical vicinal diols reveal that –OH group that becomes protonated and leaves in the one that gives rise to more stable carbocation. Acid-catalyzed conversion of Pinacol to pinacolone followed by four step mechanism as follows,

Step 1: Add proton (protonation of Pinacol using acid catalyst).

Step 2: Break a bond to give a stable molecules or ions (formation of carbocation).

Step 3: 1, 2-shift (migration of substituent from α- to β- carbon).

Step 4: deprotonation occurs (take a proton away).

(b)

Interpretation Introduction

Interpretation:

β- Aminoalcohol that gives cyclohexanecarbaldehyde has to be suggested.

Concept Introduction:

Tiffeneau–Demjanov reaction: It is an organic reaction where 1-aminomethyl-cycloalkanol gets converted to an enlarged cycloketone by reacting with nitrous acid.

Expert Solution & Answer

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Answer 5

Chapter 23, Problem 23.37P

(a)

Interpretation Introduction

Interpretation:

Similarities between the mechanism of deamination of β- aminoalcohol using nitrous acid and Pinacol rearrangement has to be given.

Concept Introduction:

Tiffeneau–Demjanov reaction: It is an organic reaction where 1-aminomethyl-cycloalkanol gets converted to an enlarged cycloketone by reacting with nitrous acid.

Pinacol rearrangement: For all glycols Pinacol rearrangement occurs. Unsymmetrical vicinal diols reveal that –OH group that becomes protonated and leaves in the one that gives rise to more stable carbocation. Acid-catalyzed conversion of Pinacol to pinacolone followed by four step mechanism as follows,

Step 1: Add proton (protonation of Pinacol using acid catalyst).

Step 2: Break a bond to give a stable molecules or ions (formation of carbocation).

Step 3: 1, 2-shift (migration of substituent from α- to β- carbon).

Step 4: deprotonation occurs (take a proton away).

(b)

Interpretation Introduction

Interpretation:

Reason for the expansion of ring in the deamination of β- aminoalcohol using nitrous acid not in Pinacol rearrangement has to be explained.

Concept Introduction:

Tiffeneau–Demjanov reaction: It is an organic reaction where 1-aminomethyl-cycloalkanol gets converted to an enlarged cycloketone by reacting with nitrous acid.

Pinacol rearrangement: For all glycols Pinacol rearrangement occurs. Unsymmetrical vicinal diols reveal that –OH group that becomes protonated and leaves in the one that gives rise to more stable carbocation. Acid-catalyzed conversion of Pinacol to pinacolone followed by four step mechanism as follows,

Step 1: Add proton (protonation of Pinacol using acid catalyst).

Step 2: Break a bond to give a stable molecules or ions (formation of carbocation).

Step 3: 1, 2-shift (migration of substituent from α- to β- carbon).

Step 4: deprotonation occurs (take a proton away).

(b)

Interpretation Introduction

Interpretation:

β- Aminoalcohol that gives cyclohexanecarbaldehyde has to be suggested.

Concept Introduction:

Tiffeneau–Demjanov reaction: It is an organic reaction where 1-aminomethyl-cycloalkanol gets converted to an enlarged cycloketone by reacting with nitrous acid.

Answer 6

Chapter 23, Problem 23.37P

(a)

Interpretation Introduction

Interpretation:

Similarities between the mechanism of deamination of β- aminoalcohol using nitrous acid and Pinacol rearrangement has to be given.

Concept Introduction:

Tiffeneau–Demjanov reaction: It is an organic reaction where 1-aminomethyl-cycloalkanol gets converted to an enlarged cycloketone by reacting with nitrous acid.

Pinacol rearrangement: For all glycols Pinacol rearrangement occurs. Unsymmetrical vicinal diols reveal that –OH group that becomes protonated and leaves in the one that gives rise to more stable carbocation. Acid-catalyzed conversion of Pinacol to pinacolone followed by four step mechanism as follows,

Step 1: Add proton (protonation of Pinacol using acid catalyst).

Step 2: Break a bond to give a stable molecules or ions (formation of carbocation).

Step 3: 1, 2-shift (migration of substituent from α- to β- carbon).

Step 4: deprotonation occurs (take a proton away).

Answer 7

Chapter 23, Problem 23.37P

(a)

Interpretation Introduction

Interpretation:

Similarities between the mechanism of deamination of β- aminoalcohol using nitrous acid and Pinacol rearrangement has to be given.

Concept Introduction:

Tiffeneau–Demjanov reaction: It is an organic reaction where 1-aminomethyl-cycloalkanol gets converted to an enlarged cycloketone by reacting with nitrous acid.

Pinacol rearrangement: For all glycols Pinacol rearrangement occurs. Unsymmetrical vicinal diols reveal that –OH group that becomes protonated and leaves in the one that gives rise to more stable carbocation. Acid-catalyzed conversion of Pinacol to pinacolone followed by four step mechanism as follows,

Step 1: Add proton (protonation of Pinacol using acid catalyst).

Step 2: Break a bond to give a stable molecules or ions (formation of carbocation).

Step 3: 1, 2-shift (migration of substituent from α- to β- carbon).

Step 4: deprotonation occurs (take a proton away).

Answer 8

(b)

Interpretation Introduction

Interpretation:

Reason for the expansion of ring in the deamination of β- aminoalcohol using nitrous acid not in Pinacol rearrangement has to be explained.

Concept Introduction:

Tiffeneau–Demjanov reaction: It is an organic reaction where 1-aminomethyl-cycloalkanol gets converted to an enlarged cycloketone by reacting with nitrous acid.

Pinacol rearrangement: For all glycols Pinacol rearrangement occurs. Unsymmetrical vicinal diols reveal that –OH group that becomes protonated and leaves in the one that gives rise to more stable carbocation. Acid-catalyzed conversion of Pinacol to pinacolone followed by four step mechanism as follows,

Step 1: Add proton (protonation of Pinacol using acid catalyst).

Step 2: Break a bond to give a stable molecules or ions (formation of carbocation).

Step 3: 1, 2-shift (migration of substituent from α- to β- carbon).

Step 4: deprotonation occurs (take a proton away).

Answer 9

(b)

Interpretation Introduction

Interpretation:

Reason for the expansion of ring in the deamination of β- aminoalcohol using nitrous acid not in Pinacol rearrangement has to be explained.

Concept Introduction:

Tiffeneau–Demjanov reaction: It is an organic reaction where 1-aminomethyl-cycloalkanol gets converted to an enlarged cycloketone by reacting with nitrous acid.

Pinacol rearrangement: For all glycols Pinacol rearrangement occurs. Unsymmetrical vicinal diols reveal that –OH group that becomes protonated and leaves in the one that gives rise to more stable carbocation. Acid-catalyzed conversion of Pinacol to pinacolone followed by four step mechanism as follows,

Step 1: Add proton (protonation of Pinacol using acid catalyst).

Step 2: Break a bond to give a stable molecules or ions (formation of carbocation).

Step 3: 1, 2-shift (migration of substituent from α- to β- carbon).

Step 4: deprotonation occurs (take a proton away).

Answer 10

(b)

Interpretation Introduction

Interpretation:

β- Aminoalcohol that gives cyclohexanecarbaldehyde has to be suggested.

Concept Introduction:

Tiffeneau–Demjanov reaction: It is an organic reaction where 1-aminomethyl-cycloalkanol gets converted to an enlarged cycloketone by reacting with nitrous acid.

Answer 11

(b)

Interpretation Introduction

Interpretation:

β- Aminoalcohol that gives cyclohexanecarbaldehyde has to be suggested.

Concept Introduction:

Tiffeneau–Demjanov reaction: It is an organic reaction where 1-aminomethyl-cycloalkanol gets converted to an enlarged cycloketone by reacting with nitrous acid.

Answer 12

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Answer 23

Ch. 23.1 - Prob. 23.1P Ch. 23.2 - Prob. 23.2P Ch. 23.2 - Prob. 23.3P Ch. 23.2 - Prob. 23.4P Ch. 23.5 - Prob. 23.5P Ch. 23.5 - Prob. AQ Ch. 23.5 - What is the hybridization of the nitrogen in...Ch. 23.5 - Prob. CQ Ch. 23.5 - The pKas of the conjugate acids of aniline and...Ch. 23.5 - Prob. EQ

Interpretation: β- Aminoalcohol that gives cyclohexanecarbaldehyde has to be suggested. Concept Introduction: Tiffeneau–Demjanov reaction: It is an organic reaction where 1-aminomethyl-cycloalkanol gets converted to an enlarged cycloketone by reacting with nitrous acid.

Chapter 23 Solutions

Interpretation:

β- Aminoalcohol that gives cyclohexanecarbaldehyde has to be suggested.

Concept Introduction:

Tiffeneau–Demjanov reaction: It is an organic reaction where 1-aminomethyl-cycloalkanol gets converted to an enlarged cycloketone by reacting with nitrous acid.