Chapter 12, Problem 54IP

(a)

Interpretation Introduction

Interpretation:

The synthesis of the given product transformation should be identified.

Concept introduction:

Reduction: Aldehydes or ketones undergoing reduction by using reducing agent like ${\text{LAH or NaBH}}_{\text{4}}$ which provides alcohol.

Potassium tert-butoxide is a strong base, which used for the abstraction of acidic hydrogen from the molecule.

Alcohols is protected by using variety of reaction for example, Alcohols can be protected by treating with tosyl chloride in presence of base.  Similarly it can be protected by using $\text{TMSCl}$ in presence of base.

Ozonolysis:

Alkene reacts with ozone which cleaves the double bond followed by work up with dimethyl sulfide forms ketone.

(b)

Interpretation Introduction

Interpretation:

The synthesis of the given product transformation should be identified.

Concept introduction:

Reduction: Aldehydes or ketones undergoing reduction by using reducing agent like ${\text{LAH or NaBH}}_{\text{4}}$ which provides alcohol.

Potassium tert-butoxide is a strong base, which used for the abstraction of acidic hydrogen from the molecule.

The Grignard reaction:

Alkyl, vinyl, or aryl-magnesium halides ($\text{RMgX}$) is called as Grignard reagent.

Grignard reagent is reaction with carbonyl compound such as aldehyde or ketone, produces corresponding alcohol is the product and it is the one of the carbon – carbon bond forming reaction.

    

Tosylation reaction:

The alcohol is treated with any tosyl chloride (methane sulfonyl chloride) which yields tosylated product this reaction is called as alkyl tosylate and which is shown below,

(c)

Interpretation Introduction

Interpretation:

The synthesis of the given product transformation should be identified.

Concept introduction:

Oxidation: Alcohols undergoing oxidation by using oxidizing agent like PCC (Pyridinium Chlorochromate) in dichloromethane which provides aldehyde.

Alcohols undergoing oxidation by using oxidizing agent like ${\text{Na}}_{\text{2}}{\text{Cr}}_{\text{2}}{\text{O}}_{\text{7}}$(chromic acid) which provides carboxylic acid.

S_N2 reaction:

The alcohols is reaction with acids like hydrochloric acid or hydrobromic acid, the bromine atom attacks back side of the carbon atoms which is bearing alcohol group which yield the corresponding inversion product.

Tertiary alcohols undergo substitution very fast than the secondary alcohols because tertiary carbocation is more stable than the secondary carbocation than the primary carbocation.

(d)

Interpretation Introduction

Interpretation:

The synthesis of the given product transformation should be identified.

Concept introduction:

Oxidation: Alcohols undergoing oxidation by using oxidizing agent like PCC (Pyridinium Chlorochromate) in dichloromethane which provides aldehyde.

Alcohols undergoing oxidation by using oxidizing agent like ${\text{Na}}_{\text{2}}{\text{Cr}}_{\text{2}}{\text{O}}_{\text{7}}$(chromic acid) which provides carboxylic acid.

Alcohols is protected by using variety of reaction for example, Alcohols can be protected by treating with tosyl chloride in presence of base.  Similarly it can be protected by using $\text{TMSCl}$ in presence of base.

S_N2 reaction:

The alcohols is reaction with acids like hydrochloric acid or hydrobromic acid, the bromine atom attacks back side of the carbon atoms which is bearing alcohol group which yield the corresponding inversion product.

Tertiary alcohols undergo substitution very fast than the secondary alcohols because tertiary carbocation is more stable than the secondary carbocation than the primary carbocation.

The Grignard reaction:

Alkyl, vinyl, or aryl-magnesium halides ($\text{RMgX}$) is called as Grignard reagent.

Grignard reagent is reaction with carbonyl compound such as aldehyde or ketone, produces corresponding alcohol is the product and it is the one of the carbon – carbon bond forming reaction.

    

(e)

Interpretation Introduction

Interpretation:

The synthesis of the given product transformation should be identified.

Concept introduction:

Hydration:

When alkene is undergoes hydration with water in the presence of sulfuric acid which yields the alcohol. In this reaction, the water molecule will behave like a hydrogen halide to the alkene which gives the addition product this reaction is known as a hydration reaction.

  

Alkene is reaction with water in the presence of sulfuric acid, first step is proton (${\text{H}}^{\text{+}}$) addition to the double bond which forms carbocation (more stable carbocation) followed by addition of hydroxide ion (${}^{\text{-}}\text{OH}$) yields alcohol as a product. The stability of carbocation is given below, Tertiary carbocation is more stable than the secondary, secondary carbocation is more stable than primary.

  

In hydration reaction, sulfuric acid is act as a proton donor, which is the driving force of the reaction. Hydration reaction will not go without acid (sulfuric acid).

Oxidation:

Alcohols undergoing oxidation by using oxidizing agent like ${\text{Na}}_{\text{2}}{\text{Cr}}_{\text{2}}{\text{O}}_{\text{7}}$(chromic acid) which provides carboxylic acid.

(f)

Interpretation Introduction

Interpretation:

The synthesis of the given product transformation should be identified.

Concept introduction:

Hydration:

When alkene is undergoes hydration with water in the presence of sulfuric acid which yields the alcohol. In this reaction, the water molecule will behave like a hydrogen halide to the alkene which gives the addition product this reaction is known as a hydration reaction.

  

Alkene is reaction with water in the presence of sulfuric acid, first step is proton (${\text{H}}^{\text{+}}$) addition to the double bond which forms carbocation (more stable carbocation) followed by addition of hydroxide ion (${}^{\text{-}}\text{OH}$) yields alcohol as a product. The stability of carbocation is given below, Tertiary carbocation is more stable than the secondary, secondary carbocation is more stable than primary.

  

In hydration reaction, sulfuric acid is act as a proton donor, which is the driving force of the reaction. Hydration reaction will not go without acid (sulfuric acid).

Bromination:

Alcohols brominated by using ${\text{PBr}}_{\text{3}}$ which provides corresponding brominated products.

Alcohols undergoing oxidation by using oxidizing agent like ${\text{Na}}_{\text{2}}{\text{Cr}}_{\text{2}}{\text{O}}_{\text{7}}$ which provides carboxylic acid.

Potassium tert-butoxide is a strong base, which used for the abstraction of acidic hydrogen from the molecule.

The Grignard reaction:

Alkyl, vinyl, or aryl-magnesium halides ($\text{RMgX}$) is called as Grignard reagent.

Grignard reagent is reaction with carbonyl compound such as aldehyde or ketone, produces corresponding alcohol is the product and it is the one of the carbon – carbon bond forming reaction.

    

(g)

Interpretation Introduction

Interpretation:

The synthesis of the given product transformation should be identified.

Concept introduction:

Oxidation:

Alcohols undergoing oxidation by using oxidizing agent like ${\text{Na}}_{\text{2}}{\text{Cr}}_{\text{2}}{\text{O}}_{\text{7}}$(chromic acid) which provides carboxylic acid.

Hydration:

When alkene is undergoes hydration with water in the presence of sulfuric acid which yields the alcohol. In this reaction, the water molecule will behave like a hydrogen halide to the alkene which gives the addition product this reaction is known as a hydration reaction.

  

Alkene is reaction with water in the presence of sulfuric acid, first step is proton (${\text{H}}^{\text{+}}$) addition to the double bond which forms carbocation (more stable carbocation) followed by addition of hydroxide ion (${}^{\text{-}}\text{OH}$) yields alcohol as a product. The stability of carbocation is given below, Tertiary carbocation is more stable than the secondary, secondary carbocation is more stable than primary.

  

In hydration reaction, sulfuric acid is act as a proton donor, which is the driving force of the reaction. Hydration reaction will not go without acid (sulfuric acid).

The Grignard reaction:

Alkyl, vinyl, or aryl-magnesium halides ($\text{RMgX}$) is called as Grignard reagent.

Grignard reagent is reaction with carbonyl compound such as aldehyde or ketone, produces corresponding alcohol is the product and it is the one of the carbon – carbon bond forming reaction.

    

Dehydration reaction:

Removal of water molecule from the reaction when the alcohol is treated with strong acid like sulfuric acid.

  

Alcohol is reaction with concentrated sulfuric acid, first alcohol gets protonated forms carbocation (more stable carbocation) followed by elimination of proton (${\text{H}}^{\text{+}}$) yields alkene as a product. The stability of carbocation is given below,

Tertiary carbocation is more stable than the secondary, secondary carbocation is more stable than primary.

In dehydration reaction, sulfuric acid is act as a proton donor, and which is used to protonate the alcohol and makes carbocation therefore sulfuric acid is the driving force of the reaction. Dehydration reaction will not go without acid (sulfuric acid).

(h)

Interpretation Introduction

Interpretation:

The synthesis of the given product transformation should be identified.

Concept introduction:

Alcohols undergoing oxidation by using oxidizing agent like ${\text{Na}}_{\text{2}}{\text{Cr}}_{\text{2}}{\text{O}}_{\text{7}}$(chromic acid) which provides carboxylic acid.

Reduction: Aldehydes or ketones undergoing reduction by using reducing agent like ${\text{LAH or NaBH}}_{\text{4}}$ which provides alcohol.

The Grignard reaction:

Alkyl, vinyl, or aryl-magnesium halides ($\text{RMgX}$) is called as Grignard reagent.

Grignard reagent is reaction with carbonyl compound such as aldehyde or ketone, produces corresponding alcohol is the product and it is the one of the carbon – carbon bond forming reaction.

    

Kucherov Reaction:

Acetylene compounds Undergoes hydration with water which provides carbonyl compounds.

(i)

Interpretation Introduction

Interpretation:

The synthesis of the given product transformation should be identified.

Concept introduction:

Alcohols undergoing oxidation by using oxidizing agent like ${\text{Na}}_{\text{2}}{\text{Cr}}_{\text{2}}{\text{O}}_{\text{7}}$(chromic acid) which provides carboxylic acid.

Potassium tert-butoxide is a strong base, which used for the abstraction of acidic hydrogen from the molecule.

Hydration:

When alkene is undergoes hydration with water in the presence of sulfuric acid which yields the alcohol. In this reaction, the water molecule will behave like a hydrogen halide to the alkene which gives the addition product this reaction is known as a hydration reaction.

  

Alkene is reaction with water in the presence of sulfuric acid, first step is proton (${\text{H}}^{\text{+}}$) addition to the double bond which forms carbocation (more stable carbocation) followed by addition of hydroxide ion (${}^{\text{-}}\text{OH}$) yields alcohol as a product. The stability of carbocation is given below, Tertiary carbocation is more stable than the secondary, secondary carbocation is more stable than primary.

  

In hydration reaction, sulfuric acid is act as a proton donor, which is the driving force of the reaction. Hydration reaction will not go without acid (sulfuric acid).

The Grignard reaction:

Alkyl, vinyl, or aryl-magnesium halides ($\text{RMgX}$) is called as Grignard reagent.

Grignard reagent is reaction with carbonyl compound such as aldehyde or ketone, produces corresponding alcohol is the product and it is the one of the carbon – carbon bond forming reaction.

    

(j)

Interpretation Introduction

Interpretation:

The synthesis of the given product transformation should be identified.

Concept introduction:

The Grignard reaction:

Alkyl, vinyl, or aryl-magnesium halides ($\text{RMgX}$) is called as Grignard reagent.

Grignard reagent is reaction with carbonyl compound such as aldehyde or ketone, produces corresponding alcohol is the product and it is the one of the carbon – carbon bond forming reaction.

    

(k)

Interpretation Introduction

Interpretation:

The synthesis of the given product transformation should be identified.

Concept introduction:

Reduction: Aldehydes or ketones undergoing reduction by using reducing agent like ${\text{LAH or NaBH}}_{\text{4}}$ which provides alcohol.

Dehydration reaction:

Removal of water molecule from the reaction when the alcohol is treated with strong acid like sulfuric acid.

  

Alcohol is reaction with concentrated sulfuric acid, first alcohol gets protonated forms carbocation (more stable carbocation) followed by elimination of proton (${\text{H}}^{\text{+}}$) yields alkene as a product. The stability of carbocation is given below,

Tertiary carbocation is more stable than the secondary, secondary carbocation is more stable than primary.

In dehydration reaction, sulfuric acid is act as a proton donor, and which is used to protonate the alcohol and makes carbocation therefore sulfuric acid is the driving force of the reaction. Dehydration reaction will not go without acid (sulfuric acid).

(l)

Interpretation Introduction

Interpretation:

The synthesis of the given product transformation should be identified.

Concept introduction:

Reduction: Aldehydes or ketones undergoing reduction by using reducing agent like ${\text{LAH or NaBH}}_{\text{4}}$ which provides alcohol.

Potassium tert-butoxide is a strong base, which used for the abstraction of acidic hydrogen from the molecule.

Tosylation reaction:

The alcohol is treated with any tosyl chloride (methane sulfonyl chloride) which yields tosylated product this reaction is called as alkyl tosylate and which is shown below,

(m)

Interpretation Introduction

Interpretation:

The synthesis of the given product transformation should be identified.

Concept introduction

Reduction: Aldehydes or ketones undergoing reduction by using reducing agent like ${\text{LAH or NaBH}}_{\text{4}}$ which provides alcohol.

Potassium tert-butoxide is a strong base, which used for the abstraction of acidic hydrogen from the molecule.

Tosylation reaction:

The alcohol is treated with any tosyl chloride (methane sulfonyl chloride) which yields tosylated product this reaction is called as alkyl tosylate and which is shown below,

Hydroboration:

Hydroboration is the addition of a hydrogen-boron bond to the Carbon-Carbon, Carbon-Nitrogen, and Carbon-Oxygen double bonds and Carbon-Carbon triple bonds.

When alkene undergoes hydroboration using alkyl borane and hydrogen peroxide followed by hydrolysis which yields the alcohol. The formation of alcohol is depends on the less hindered carbon of the double bond.

(n)

Interpretation Introduction

Interpretation:

The synthesis of the given product transformation should be identified.

Concept introduction:

The Grignard reaction:

Alkyl, vinyl, or aryl-magnesium halides ($\text{RMgX}$) is called as Grignard reagent.

Grignard reagent is reaction with carbonyl compound such as aldehyde or ketone, produces corresponding alcohol is the product and it is the one of the carbon – carbon bond forming reaction.

    

Dehydration reaction:

Removal of water molecule from the reaction when the alcohol is treated with strong acid like sulfuric acid.

  

Alcohol is reaction with concentrated sulfuric acid, first alcohol gets protonated forms carbocation (more stable carbocation) followed by elimination of proton (${\text{H}}^{\text{+}}$) yields alkene as a product. The stability of carbocation is given below,

Tertiary carbocation is more stable than the secondary, secondary carbocation is more stable than primary.

In dehydration reaction, sulfuric acid is act as a proton donor, and which is used to protonate the alcohol and makes carbocation therefore sulfuric acid is the driving force of the reaction. Dehydration reaction will not go without acid (sulfuric acid).

(o)

Interpretation Introduction

Interpretation:

The synthesis of the given product transformation should be identified.

Concept introduction:

The Grignard reaction:

Alkyl, vinyl, or aryl-magnesium halides ($\text{RMgX}$) is called as Grignard reagent.

Grignard reagent is reaction with carbonyl compound such as aldehyde or ketone, produces corresponding alcohol is the product and it is the one of the carbon – carbon bond forming reaction.

    

(p)

Interpretation Introduction

Interpretation:

The synthesis of the given product transformation should be identified.

Concept introduction:

Bromination:

Alcohols are reaction with PBr₃ in pyridine which undergoes S_N2 type of reaction, the bromine attacks the carbon atom through the back side and provides Inverse brominated compound.

Reduction: Aldehydes or ketones undergoing reduction by using reducing agent like ${\text{LAH or NaBH}}_{\text{4}}$ which provides alcohol.

(q)

Interpretation Introduction

Interpretation:

The synthesis of the given product transformation should be identified.

Concept introduction:

Hydroboration:

Hydroboration is the addition of a hydrogen-boron bond to the Carbon-Carbon, Carbon-Nitrogen, and Carbon-Oxygen double bonds and Carbon-Carbon triple bonds.

When alkene undergoes hydroboration using alkyl borane and hydrogen peroxide followed by hydrolysis which yields the alcohol. The formation of alcohol is depends on the less hindered carbon of the double bond.

Oxidation: Alcohols undergoing oxidation by using oxidizing agent like PCC (Pyridinium Chlorochromate) in dichloromethane which provides aldehyde.

Alcohols undergoing oxidation by using oxidizing agent like ${\text{Na}}_{\text{2}}{\text{Cr}}_{\text{2}}{\text{O}}_{\text{7}}$(chromic acid) which provides carboxylic acid.

The Grignard reaction:

Alkyl, vinyl, or aryl-magnesium halides ($\text{RMgX}$) is called as Grignard reagent.

Grignard reagent is reaction with carbonyl compound such as aldehyde or ketone, produces corresponding alcohol is the product and it is the one of the carbon – carbon bond forming reaction.