Chapter 22, Problem 22.78P

Interpretation Introduction

(a)

Interpretation: The structural features that give docetaxel a better water solubility profile are to be predicted.

Concept introduction: The solubility of solute in solution depends upon the polarity of solute and solvent. The solute and solvent of same polarity are soluble with each other and insoluble if the polarity is different.

Interpretation Introduction

(b)

Interpretation: Three more resonance structures of carbamate are to be drawn and the resonance structures are to be ranked in order of increasing stability.

Concept introduction: The delocalization of lone pair or free electrons from one atom to another atom is known as resonance. The stability of compound depends upon the number of resonating structures. More the resonating structures of a compound, more will its stability.

Interpretation Introduction

(c)

Interpretation: A stepwise mechanism for the hydrolysis of a carbamate with a tert-butoxy group is to be drawn.

Concept introduction: The replacement or substitution of one functional group with another functional group in any chemical reaction is termed as substitution reaction. The electron rich chemical species that contains negative charge or lone pair of electrons is known as a nucleophile. In nucleophilc acyl substitution reaction, a nucleophile takes the position of a leaving group.

Interpretation Introduction

(d)

Interpretation: The products formed by the hydrolysis of docetaxel with aqueous acid are to be drawn.

Concept introduction: The hydrolysis of ester bond under acidic conditions leads to the formation of two compounds, one that has alcoholic group $\left(\text{OH}\right)$ and another that has $\left(\text{COOH}\right)$ group.