Determining order of reactivity

Question

Assignment:

Q1. Select an alkyl halide and a nucleophile that will give each of the following products:

a. CH₃C≡CCH₂CH₃

b. CH₃CH₂OCH₂CH₃

c. CH₃CH₂SCH₃

d. (CH₃)₂CHCH₂OH

Q2. Draw out each of the following equations in a way that shows clearly the stereochemistry of the reactants and products.

a. (R)-3-chlorohexane+sodium methoxide(in methanol) → ^Sn2 → 3-methoxyhexane

b. (S)-2-chlorobutane+methanol → ^Sn2→ 2-methoxybutane

Q3. Determine the order of reactivity for (CH₃)₂CHCH₂Br, (CH₃)₃CBr, and CH₃CHBrCH₂CH₃

Reacting with

a. CH₃OH(methanol)

b. NaSH(sodium hydrosulfide)

Q4. Tell all possible products you expect and by what mechanism they are formed for each of the following reactions:

a. 2-chlorohexane+ethanol →

b. 2-chlorohexane+sodiumethoxide(inethanol) →

c. 2-chlorohexane+sodiumhydrosulfide →

5. Give the structures of all possible products when 2-chlorobutane reacts by the E-2 mechanism.

Provide complete and step by step solution for the question and show calculations and use formulas.