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Chapter 7: PROBLEM 7.41 (page 290)

Question: Draw the products formed when each alkyl halide is treated with NaCN.

a.

b.

Short Answer

Expert verified

Deduce the chemical structure from the given ball-and-stick model using the number of bonds attached to the particular ball.

Step by step solution

01

Ball-and-stick model

Deduce the chemical structure from the given ball-and-stick model using the number of bonds attached to the particular ball.

02

Nucleophilic substitution reactions

The base or the nucleophile replaces the halide ion from the alkyl halide

03

Products of the given reactions

In each of the given compounds, the given black balls are tetravalent and must be symbolizing the carbon atoms. The given white balls are single-bonded and must be hydrogen atoms.

The red ball is single-bonded and much larger than the carbon atoms. The red ball must be symbolizing the bromine atom.

In each of the following reactions, CN-being the stronger nucleophile substitutes the bromine atom via the SN2 mechanism.

a. When compound (a) is treated with NaCN, inversion of symmetry takes place; the CN- ion attacks the alkyl halide from the opposite side of the halide atom. Thus, the skeletal structure of the compound is formed, which is shown below:

b. When compound (a) is treated with NaCN, inversion of symmetry takes place; the CN- ion attacks the alkyl halide from the opposite side of the halide atom. Thus, the skeletal structure of the compound is formed, which is shown below:

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Most popular questions from this chapter

Question: Fluticasone, the chapter-opening molecule, can be prepared by the following reaction. Draw a stepwise mechanism for this reaction.

Question: What nucleophile is needed to convert to each product?

a.


b.


c.

d.

Question: Draw the products of each reaction and indicate the stereochemistry where appropriate.

a.

b.

c.

Question: Consider the following SN1 reaction.

  1. Draw a mechanism for this reaction using curved arrows.
  2. Draw an energy diagram. Label the axes, starting material, product Eaand ∆H°. Assume that the starting material and product are equal in energy.
  3. Draw the structure of any transition states.
  4. What is the rate equation for this reaction?
  5. What happens to the reaction rate in each of the following instances? [1] The leaving group is changed from I- to Cl-;[2] The solvent is changed from H2O to DMF; [3] The alkyl halide is changed from (CH3)2 C(I) CH2CH3 to (CH3) CHCH(I)CH3 ; [4] The concentration of H2O is increased by a factor of five; and [5] The concentrations of both the alkyl halide and H2O are increased by factor of five.

Question: What happens to the rate of an SN2 reaction under each of the following conditions?

a. [RX] is tripled, and:Nu- stays the same.

b. Both [RX] and role="math" localid="1648206216789" :Nu-are tripled.

c. [RX] is halved, androle="math" localid="1648206048742" :Nu-stays the same.

d. [RX] is halved, and role="math" localid="1648206067374" :Nu-is doubled.
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