Question

1) Describe the reaction that occurs at modest temperatures between the starting material and nucleophile, base or solvent indicated below the arrow using chemical formulas. Draw the corresponding energy/reaction coordinate diagram. What is/are the major reaction product(s)? What is the rate determining step of this reaction? What rate law follows this reaction?

Answer 1

Here's what I get

Step-by-step explanation:

(a) There will be an equilibrium between propoxide and isopropyl alcohol.

CH₃CH₂CH₂O⁻ + (CH₃)₂CHO-H ⇌ CH₃CH₂CH₂OH + (CH₃)₂CHO⁻

The isopropoxide is the more basic ion, so it will be the better base and the better nucleophile.

(b) There is always a competition between substitution and elimination.

However, the temperature is moderate, so substitution will predominate.

(c) Attack on the substrate will occur at C-3, for two reasons:

• I is a better leaving group than Br.
• C-3 is 3°, while C-1 is 1°.

(d) The reaction will be an SN1 displacement reaction. The energy/reaction coordinate diagram is below.

(e) The rate-determining step is the first step — ionization of the alkyl iodide.

(f)The rate law is rate = k[R-I]

(g) The major product will be 1-bromo-3-methyl-3-(propan-2-yloxy)pentane.