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Chapter 7: PROBLEM 7.22 (page 268)

Question: What neutral nucleophile is needed to convert C to D? Imatinib, an effective treatment for certain cancers, is prepared in one step from D.

Short Answer

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Answer

The neutral nucleophile that is needed to convert C to D is given below:

Step by step solution

01

Neutral nucleophile

Nucleophiles that do not possess a charge are referred to as neutral nucleophiles. Some examples of neutral nucleophiles include , R-OH and R-O-R.

02

Imatinib

Imatinib belongs to the category of medication “kinase inhibitor.”

It can cure certain kinds of cancer and other conditions like gastrointestinal stromal tumors and acute lymphocytic leukemia.

03

Determination of neutral nucleophile that is needed to convert C to D

The neutral nucleophile that is required to transform C to D is:

Neutral nucleophile that is required to transform C to D

The chlorine atom of compound C is replaced by a nitrogen atom through a new group. This indicates that a substitution reaction is also taking place within the reaction. The lone pair of electrons on the nitrogen atom strikes the electron-deficient atom to form product D as:

Transformation of compound C to compound D

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Most popular questions from this chapter

Question: Identify the stronger nucleophile in each pair of anions.

a. Br- or Cl- in a polar protic solvent.

b. OH-or Cl- in a polar aprotic solvent.

c. HS- or F- in a polar protic solvent.

Question: Draw the eight constitutional isomers having the molecular formula C5H11Cl .

  1. Give the IUPAC name for each compound (ignoring R and S designations).
  2. Classify each alkyl halide as 1°,2°or3°.
  3. Label any stereogenic centers.
  4. For each constitutional isomer that contains a stereogenic center, draw all possible stereoisomers, and label each stereogenic center as R or S.

Question: Draw an energy diagram for the following SN2 reaction. Label the axes, the starting materials, and the product. Draw the structure of the transition state.

Question: Rank the following carbocations in order of increasing stability.

a.

b.

c.

Question: Draw the products of each SN1 reaction and indicate the stereochemistry when necessary.

a.

b.
See all solutions

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