A mechanism has to be proposed for the given acid-catalyzed formation of the ethoxyethyl protecting group. Concept introduction: Hydrolysis is a chemical process in which a molecule is cleaved into two parts by the addition of a molecule of water. If the reaction is carried out with the help of an acid it is said to be an acid catalyzed hydrolysis. Mechanism of the reaction is the step-by-step description of the process by which reactants are changed into products. Curved arrows show the bonds that are formed and the bonds that are broken in a reaction. Curved arrows used to understand a reaction mechanism. Electrophile: It is positively charged species which seeks for negative charge and hence accepts pair of electrons from negatively charged species (Nucleophiles) which results in the formation of chemical bond . Nucleophile: It is negatively charged species which seeks for positive charge and hence donate pair of electrons to positively charged species (electrophiles) which results in the formation of chemical bond.

Question

Choose the best explanation for why these compounds are all less than fifteen carbons. A) Aldehydes with longer alkyl chains become increasingly nonpolar and the LDF are stronger than hydrogen bonding with ethanol. B) Ethanol molecules will hydrogen bond with the oxygen of the aldehydes. However, longer alkyl chains interrupt the ability of the aldehyde to hydrogen bond with ethanol which decreases the solubility. C) Ethanol molecules will form strong LDF interactions between the alkyl chains of the aldehydes and the alkyl groups of ethanol. The strong attractions cause the aldehydes to precipitate out of solution. D) When aldehydes chain length increases, the aldehydes have stronger intermolecular force with the small ethanol solvent molecules than the ethanol-ethanol intermolecular force.

Answer 1

Question

Chapter 16, Problem 16.63P

(a)

Interpretation Introduction

Interpretation: A mechanism has to be proposed for the given acid-catalyzed formation of the ethoxyethyl protecting group.

Concept introduction:

Hydrolysis is a chemical process in which a molecule is cleaved into two parts by the addition of a molecule of water. If the reaction is carried out with the help of an acid it is said to be an acid catalyzed hydrolysis.

Mechanism of the reaction is the step-by-step description of the process by which reactants are changed into products.

Curved arrows show the bonds that are formed and the bonds that are broken in a reaction.

Curved arrows used to understand a reaction mechanism.

Electrophile: It is positively charged species which seeks for negative charge and hence accepts pair of electrons from negatively charged species (Nucleophiles) which results in the formation of chemical bond.

Nucleophile: It is negatively charged species which seeks for positive charge and hence donate pair of electrons to positively charged species (electrophiles) which results in the formation of chemical bond.

(b)

Interpretation Introduction

Interpretation: An experimental procedure has to be suggested whereby the protecting group in the reaction can be removed to regenerate the unprotected alcohol.

Concept introduction:

Hydrolysis is a chemical process in which a molecule is cleaved into two parts by the addition of a molecule of water. If the reaction is carried out with the help of an acid it is said to be an acid catalyzed hydrolysis.

Mechanism of the reaction is the step-by-step description of the process by which reactants are changed into products.

Curved arrows show the bonds that are formed and the bonds that are broken in a reaction.

Curved arrows used to understand a reaction mechanism.

Electrophile: It is positively charged species which seeks for negative charge and hence accepts pair of electrons from negatively charged species (Nucleophiles) which results in the formation of chemical bond.

Nucleophile: It is negatively charged species which seeks for positive charge and hence donate pair of electrons to positively charged species (electrophiles) which results in the formation of chemical bond.

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Choose the best explanation for why these compounds are all less than fifteen carbons. A) Aldehydes with longer alkyl chains become increasingly nonpolar and the LDF are stronger than hydrogen bonding with ethanol. B) Ethanol molecules will hydrogen bond with the oxygen of the aldehydes. However, longer alkyl chains interrupt the ability of the aldehyde to hydrogen bond with ethanol which decreases the solubility. C) Ethanol molecules will form strong LDF interactions between the alkyl chains of the aldehydes and the alkyl groups of ethanol. The strong attractions cause the aldehydes to precipitate out of solution. D) When aldehydes chain length increases, the aldehydes have stronger intermolecular force with the small ethanol solvent molecules than the ethanol-ethanol intermolecular force.

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