Using curved arrows indicate the flow of electrons for the given mechanism. Concept introduction: Nucleophile: Nucleophiles are electron rich compounds which donates electrons to electrophilic compounds which results in bond formation. Nucleophilic nature depends on the negative charge present in the molecule, the solvent in which it present and the electronegativity of the atom. Electrophile: Electrophiles are electron deficient compounds which accepts electrons from nucleophiles that results in bond formation. Chemical reaction involves bond making and breaking of two or more reactants in order to attain products from the reactants. Addition Reaction: It is defined as chemical reaction in which two given molecules combines and forms product. The types of addition reactions are electrophilic addition, nucleophilic addition, free radical additions and cycloadditions. Generally, compounds with carbon-hetero atom bonds favors addition reaction. In addition reaction of alkenes when two substituents are placed on same side of C = C then it is named as s y n addition if it is placed on opposite sides of C = C it is defined as anti-addition. Acid Catalyzed Hydration Reaction: The reaction involves breaking of phi bonds between carbon-carbon multiple bonds and addition of alcohol to more substituted position of carbon in the molecule. First step is the acid donates proton to the alkene which leads to the formation of more stable carbo cation. Then, the water is added to the given alkene through acid catalyzed reaction where the water gets added to the carbo cation finally, the removal of one proton from oxonium ion (oxygen with one positive charge) using water results in the formation of product.

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Answer 1

Question

Chapter 6, Problem 69P

(a)

Interpretation Introduction

Interpretation:

Using curved arrows indicate the flow of electrons for the given mechanism.

Concept introduction:

Nucleophile: Nucleophiles are electron rich compounds which donates electrons to electrophilic compounds which results in bond formation.

Nucleophilic nature depends on the negative charge present in the molecule, the solvent in which it present and the electronegativity of the atom.

Electrophile: Electrophiles are electron deficient compounds which accepts electrons from nucleophiles that results in bond formation.

Chemical reaction involves bond making and breaking of two or more reactants in order to attain products from the reactants.

Addition Reaction: It is defined as chemical reaction in which two given molecules combines and forms product. The types of addition reactions are electrophilic addition, nucleophilic addition, free radical additions and cycloadditions. Generally, compounds with carbon-hetero atom bonds favors addition reaction.

In addition reaction of alkenes when two substituents are placed on same side of C=C then it is named as syn addition if it is placed on opposite sides of C=C it is defined as anti-addition.

Acid Catalyzed Hydration Reaction: The reaction involves breaking of phi bonds between carbon-carbon multiple bonds and addition of alcohol to more substituted position of carbon in the molecule.

First step is the acid donates proton to the alkene which leads to the formation of more stable carbo cation.

Then, the water is added to the given alkene through acid catalyzed reaction where the water gets added to the carbo cation finally, the removal of one proton from oxonium ion (oxygen with one positive charge) using water results in the formation of product.

(b)

Interpretation Introduction

Interpretation:

The reaction coordinate diagram for the given reaction should be determined.

Concept introduction:

Addition Reaction: It is defined as chemical reaction in which two given molecules combines and forms product. The types of addition reactions are electrophilic addition, nucleophilic addition, free radical additions and cycloadditions. Generally, compounds with carbon-hetero atom bonds favors addition reaction.

In addition reaction of alkenes when two substituents are placed on same side of C=C then it is named as syn addition if it is placed on opposite sides of C=C it is defined as anti-addition.

Acid Catalyzed Hydration Reaction: The reaction involves breaking of phi bonds between carbon-carbon multiple bonds and addition of alcohol to more substituted position of carbon in the molecule.

First step is the acid donates proton to the alkene which leads to the formation of more stable carbo cation.

Then, the water is added to the given alkene through acid catalyzed reaction where the water gets added to the carbo cation finally, the removal of one proton from oxonium ion (oxygen with one positive charge) using water results in the formation of product.

Carbocation: it is carbon ion that bears a positive charge on it.

Carbocation stability order:

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4. Provide a clear arrow-pushing mechanism for each of the following reactions. Do not skip proton transfers, do not combine steps, and make sure your arrows are clear enough to be interpreted without ambiguity. a. 2. 1. LDA 3. H3O+ HO

b. H3C CH3 H3O+ ✓ H OH

2. Provide reagents/conditions to accomplish the following syntheses. More than one step is required in some cases. a. CH3

Answer 2

Question

Chapter 6, Problem 69P

(a)

Interpretation Introduction

Interpretation:

Using curved arrows indicate the flow of electrons for the given mechanism.

Concept introduction:

Nucleophile: Nucleophiles are electron rich compounds which donates electrons to electrophilic compounds which results in bond formation.

Nucleophilic nature depends on the negative charge present in the molecule, the solvent in which it present and the electronegativity of the atom.

Electrophile: Electrophiles are electron deficient compounds which accepts electrons from nucleophiles that results in bond formation.

Chemical reaction involves bond making and breaking of two or more reactants in order to attain products from the reactants.

Addition Reaction: It is defined as chemical reaction in which two given molecules combines and forms product. The types of addition reactions are electrophilic addition, nucleophilic addition, free radical additions and cycloadditions. Generally, compounds with carbon-hetero atom bonds favors addition reaction.

In addition reaction of alkenes when two substituents are placed on same side of C=C then it is named as syn addition if it is placed on opposite sides of C=C it is defined as anti-addition.

Acid Catalyzed Hydration Reaction: The reaction involves breaking of phi bonds between carbon-carbon multiple bonds and addition of alcohol to more substituted position of carbon in the molecule.

First step is the acid donates proton to the alkene which leads to the formation of more stable carbo cation.

Then, the water is added to the given alkene through acid catalyzed reaction where the water gets added to the carbo cation finally, the removal of one proton from oxonium ion (oxygen with one positive charge) using water results in the formation of product.

(b)

Interpretation Introduction

Interpretation:

The reaction coordinate diagram for the given reaction should be determined.

Concept introduction:

Addition Reaction: It is defined as chemical reaction in which two given molecules combines and forms product. The types of addition reactions are electrophilic addition, nucleophilic addition, free radical additions and cycloadditions. Generally, compounds with carbon-hetero atom bonds favors addition reaction.

In addition reaction of alkenes when two substituents are placed on same side of C=C then it is named as syn addition if it is placed on opposite sides of C=C it is defined as anti-addition.

Acid Catalyzed Hydration Reaction: The reaction involves breaking of phi bonds between carbon-carbon multiple bonds and addition of alcohol to more substituted position of carbon in the molecule.

First step is the acid donates proton to the alkene which leads to the formation of more stable carbo cation.

Then, the water is added to the given alkene through acid catalyzed reaction where the water gets added to the carbo cation finally, the removal of one proton from oxonium ion (oxygen with one positive charge) using water results in the formation of product.

Carbocation: it is carbon ion that bears a positive charge on it.

Carbocation stability order:

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Answer 3

Question

Chapter 6, Problem 69P

(a)

Interpretation Introduction

Interpretation:

Using curved arrows indicate the flow of electrons for the given mechanism.

Concept introduction:

Nucleophile: Nucleophiles are electron rich compounds which donates electrons to electrophilic compounds which results in bond formation.

Nucleophilic nature depends on the negative charge present in the molecule, the solvent in which it present and the electronegativity of the atom.

Electrophile: Electrophiles are electron deficient compounds which accepts electrons from nucleophiles that results in bond formation.

Chemical reaction involves bond making and breaking of two or more reactants in order to attain products from the reactants.

Addition Reaction: It is defined as chemical reaction in which two given molecules combines and forms product. The types of addition reactions are electrophilic addition, nucleophilic addition, free radical additions and cycloadditions. Generally, compounds with carbon-hetero atom bonds favors addition reaction.

In addition reaction of alkenes when two substituents are placed on same side of C=C then it is named as syn addition if it is placed on opposite sides of C=C it is defined as anti-addition.

Acid Catalyzed Hydration Reaction: The reaction involves breaking of phi bonds between carbon-carbon multiple bonds and addition of alcohol to more substituted position of carbon in the molecule.

First step is the acid donates proton to the alkene which leads to the formation of more stable carbo cation.

Then, the water is added to the given alkene through acid catalyzed reaction where the water gets added to the carbo cation finally, the removal of one proton from oxonium ion (oxygen with one positive charge) using water results in the formation of product.

(b)

Interpretation Introduction

Interpretation:

The reaction coordinate diagram for the given reaction should be determined.

Concept introduction:

Addition Reaction: It is defined as chemical reaction in which two given molecules combines and forms product. The types of addition reactions are electrophilic addition, nucleophilic addition, free radical additions and cycloadditions. Generally, compounds with carbon-hetero atom bonds favors addition reaction.

In addition reaction of alkenes when two substituents are placed on same side of C=C then it is named as syn addition if it is placed on opposite sides of C=C it is defined as anti-addition.

Acid Catalyzed Hydration Reaction: The reaction involves breaking of phi bonds between carbon-carbon multiple bonds and addition of alcohol to more substituted position of carbon in the molecule.

First step is the acid donates proton to the alkene which leads to the formation of more stable carbo cation.

Then, the water is added to the given alkene through acid catalyzed reaction where the water gets added to the carbo cation finally, the removal of one proton from oxonium ion (oxygen with one positive charge) using water results in the formation of product.

Carbocation: it is carbon ion that bears a positive charge on it.

Carbocation stability order:

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Answer 4

Question

Chapter 6, Problem 69P

(a)

Interpretation Introduction

Interpretation:

Using curved arrows indicate the flow of electrons for the given mechanism.

Concept introduction:

Nucleophile: Nucleophiles are electron rich compounds which donates electrons to electrophilic compounds which results in bond formation.

Nucleophilic nature depends on the negative charge present in the molecule, the solvent in which it present and the electronegativity of the atom.

Electrophile: Electrophiles are electron deficient compounds which accepts electrons from nucleophiles that results in bond formation.

Chemical reaction involves bond making and breaking of two or more reactants in order to attain products from the reactants.

Addition Reaction: It is defined as chemical reaction in which two given molecules combines and forms product. The types of addition reactions are electrophilic addition, nucleophilic addition, free radical additions and cycloadditions. Generally, compounds with carbon-hetero atom bonds favors addition reaction.

In addition reaction of alkenes when two substituents are placed on same side of C=C then it is named as syn addition if it is placed on opposite sides of C=C it is defined as anti-addition.

Acid Catalyzed Hydration Reaction: The reaction involves breaking of phi bonds between carbon-carbon multiple bonds and addition of alcohol to more substituted position of carbon in the molecule.

First step is the acid donates proton to the alkene which leads to the formation of more stable carbo cation.

Then, the water is added to the given alkene through acid catalyzed reaction where the water gets added to the carbo cation finally, the removal of one proton from oxonium ion (oxygen with one positive charge) using water results in the formation of product.

(b)

Interpretation Introduction

Interpretation:

The reaction coordinate diagram for the given reaction should be determined.

Concept introduction:

Addition Reaction: It is defined as chemical reaction in which two given molecules combines and forms product. The types of addition reactions are electrophilic addition, nucleophilic addition, free radical additions and cycloadditions. Generally, compounds with carbon-hetero atom bonds favors addition reaction.

In addition reaction of alkenes when two substituents are placed on same side of C=C then it is named as syn addition if it is placed on opposite sides of C=C it is defined as anti-addition.

Acid Catalyzed Hydration Reaction: The reaction involves breaking of phi bonds between carbon-carbon multiple bonds and addition of alcohol to more substituted position of carbon in the molecule.

First step is the acid donates proton to the alkene which leads to the formation of more stable carbo cation.

Then, the water is added to the given alkene through acid catalyzed reaction where the water gets added to the carbo cation finally, the removal of one proton from oxonium ion (oxygen with one positive charge) using water results in the formation of product.

Carbocation: it is carbon ion that bears a positive charge on it.

Carbocation stability order:

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Answer 5

Chapter 6, Problem 69P

(a)

Interpretation Introduction

Interpretation:

Using curved arrows indicate the flow of electrons for the given mechanism.

Concept introduction:

Nucleophile: Nucleophiles are electron rich compounds which donates electrons to electrophilic compounds which results in bond formation.

Nucleophilic nature depends on the negative charge present in the molecule, the solvent in which it present and the electronegativity of the atom.

Electrophile: Electrophiles are electron deficient compounds which accepts electrons from nucleophiles that results in bond formation.

Chemical reaction involves bond making and breaking of two or more reactants in order to attain products from the reactants.

Addition Reaction: It is defined as chemical reaction in which two given molecules combines and forms product. The types of addition reactions are electrophilic addition, nucleophilic addition, free radical additions and cycloadditions. Generally, compounds with carbon-hetero atom bonds favors addition reaction.

In addition reaction of alkenes when two substituents are placed on same side of C=C then it is named as syn addition if it is placed on opposite sides of C=C it is defined as anti-addition.

Acid Catalyzed Hydration Reaction: The reaction involves breaking of phi bonds between carbon-carbon multiple bonds and addition of alcohol to more substituted position of carbon in the molecule.

First step is the acid donates proton to the alkene which leads to the formation of more stable carbo cation.

Then, the water is added to the given alkene through acid catalyzed reaction where the water gets added to the carbo cation finally, the removal of one proton from oxonium ion (oxygen with one positive charge) using water results in the formation of product.

(b)

Interpretation Introduction

Interpretation:

The reaction coordinate diagram for the given reaction should be determined.

Concept introduction:

Addition Reaction: It is defined as chemical reaction in which two given molecules combines and forms product. The types of addition reactions are electrophilic addition, nucleophilic addition, free radical additions and cycloadditions. Generally, compounds with carbon-hetero atom bonds favors addition reaction.

In addition reaction of alkenes when two substituents are placed on same side of C=C then it is named as syn addition if it is placed on opposite sides of C=C it is defined as anti-addition.

Acid Catalyzed Hydration Reaction: The reaction involves breaking of phi bonds between carbon-carbon multiple bonds and addition of alcohol to more substituted position of carbon in the molecule.

First step is the acid donates proton to the alkene which leads to the formation of more stable carbo cation.

Then, the water is added to the given alkene through acid catalyzed reaction where the water gets added to the carbo cation finally, the removal of one proton from oxonium ion (oxygen with one positive charge) using water results in the formation of product.

Carbocation: it is carbon ion that bears a positive charge on it.

Carbocation stability order:

Answer 6

Chapter 6, Problem 69P

(a)

Interpretation Introduction

Interpretation:

Using curved arrows indicate the flow of electrons for the given mechanism.

Concept introduction:

Nucleophile: Nucleophiles are electron rich compounds which donates electrons to electrophilic compounds which results in bond formation.

Nucleophilic nature depends on the negative charge present in the molecule, the solvent in which it present and the electronegativity of the atom.

Electrophile: Electrophiles are electron deficient compounds which accepts electrons from nucleophiles that results in bond formation.

Chemical reaction involves bond making and breaking of two or more reactants in order to attain products from the reactants.

Addition Reaction: It is defined as chemical reaction in which two given molecules combines and forms product. The types of addition reactions are electrophilic addition, nucleophilic addition, free radical additions and cycloadditions. Generally, compounds with carbon-hetero atom bonds favors addition reaction.

In addition reaction of alkenes when two substituents are placed on same side of C=C then it is named as syn addition if it is placed on opposite sides of C=C it is defined as anti-addition.

Acid Catalyzed Hydration Reaction: The reaction involves breaking of phi bonds between carbon-carbon multiple bonds and addition of alcohol to more substituted position of carbon in the molecule.

First step is the acid donates proton to the alkene which leads to the formation of more stable carbo cation.

Then, the water is added to the given alkene through acid catalyzed reaction where the water gets added to the carbo cation finally, the removal of one proton from oxonium ion (oxygen with one positive charge) using water results in the formation of product.

Answer 7

Chapter 6, Problem 69P

(a)

Interpretation Introduction

Interpretation:

Using curved arrows indicate the flow of electrons for the given mechanism.

Concept introduction:

Nucleophile: Nucleophiles are electron rich compounds which donates electrons to electrophilic compounds which results in bond formation.

Nucleophilic nature depends on the negative charge present in the molecule, the solvent in which it present and the electronegativity of the atom.

Electrophile: Electrophiles are electron deficient compounds which accepts electrons from nucleophiles that results in bond formation.

Chemical reaction involves bond making and breaking of two or more reactants in order to attain products from the reactants.

Addition Reaction: It is defined as chemical reaction in which two given molecules combines and forms product. The types of addition reactions are electrophilic addition, nucleophilic addition, free radical additions and cycloadditions. Generally, compounds with carbon-hetero atom bonds favors addition reaction.

In addition reaction of alkenes when two substituents are placed on same side of C=C then it is named as syn addition if it is placed on opposite sides of C=C it is defined as anti-addition.

Acid Catalyzed Hydration Reaction: The reaction involves breaking of phi bonds between carbon-carbon multiple bonds and addition of alcohol to more substituted position of carbon in the molecule.

First step is the acid donates proton to the alkene which leads to the formation of more stable carbo cation.

Then, the water is added to the given alkene through acid catalyzed reaction where the water gets added to the carbo cation finally, the removal of one proton from oxonium ion (oxygen with one positive charge) using water results in the formation of product.

Answer 8

(b)

Interpretation Introduction

Interpretation:

The reaction coordinate diagram for the given reaction should be determined.

Concept introduction:

Addition Reaction: It is defined as chemical reaction in which two given molecules combines and forms product. The types of addition reactions are electrophilic addition, nucleophilic addition, free radical additions and cycloadditions. Generally, compounds with carbon-hetero atom bonds favors addition reaction.

In addition reaction of alkenes when two substituents are placed on same side of C=C then it is named as syn addition if it is placed on opposite sides of C=C it is defined as anti-addition.

Acid Catalyzed Hydration Reaction: The reaction involves breaking of phi bonds between carbon-carbon multiple bonds and addition of alcohol to more substituted position of carbon in the molecule.

First step is the acid donates proton to the alkene which leads to the formation of more stable carbo cation.

Then, the water is added to the given alkene through acid catalyzed reaction where the water gets added to the carbo cation finally, the removal of one proton from oxonium ion (oxygen with one positive charge) using water results in the formation of product.

Carbocation: it is carbon ion that bears a positive charge on it.

Carbocation stability order:

Answer 9

(b)

Interpretation Introduction

Interpretation:

The reaction coordinate diagram for the given reaction should be determined.

Concept introduction:

Addition Reaction: It is defined as chemical reaction in which two given molecules combines and forms product. The types of addition reactions are electrophilic addition, nucleophilic addition, free radical additions and cycloadditions. Generally, compounds with carbon-hetero atom bonds favors addition reaction.

In addition reaction of alkenes when two substituents are placed on same side of C=C then it is named as syn addition if it is placed on opposite sides of C=C it is defined as anti-addition.

Acid Catalyzed Hydration Reaction: The reaction involves breaking of phi bonds between carbon-carbon multiple bonds and addition of alcohol to more substituted position of carbon in the molecule.

First step is the acid donates proton to the alkene which leads to the formation of more stable carbo cation.

Then, the water is added to the given alkene through acid catalyzed reaction where the water gets added to the carbo cation finally, the removal of one proton from oxonium ion (oxygen with one positive charge) using water results in the formation of product.

Carbocation: it is carbon ion that bears a positive charge on it.

Carbocation stability order:

Answer 10

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Answer 11

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Answer 12

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Answer 13

Ch. 6.1 - Draw the mechanism for the reaction of cyclohexene...Ch. 6.2 - a. How many bond orbitals are avilable for...Ch. 6.2 - Prob. 3P Ch. 6.2 - Prob. 4P Ch. 6.3 - Prob. 5P Ch. 6.4 - Prob. 6P Ch. 6.4 - Prob. 7P Ch. 6.4 - What alkene should be used to synthesize each of...Ch. 6.5 - The pKa of a protonated alcohol is about 2.5, and...Ch. 6.5 - Prob. 10P

Solution Summary: The author explains that curved arrows indicate the flow of electrons for the given mechanism.

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