Finding acid-catalyzed dehydration products

Question

Assignment:

Q1. Arrange the following compounds in order of increasing acidity, and explain the reasons for your choice of order:
a. Cyclohexanol
b. 4-chlorophenol
c. 2-fluorocyclohexanol
d. 2-nitrophenol

Q2. Show the structure of all possible acid-catalyzed dehydration products of the following. If more than one alkene is possible, predict which ones will be formed in the largest amounts:
a. 1-ethylcyclohexanol
b. 3-methyl-1-3hexanol

Q3. Write an equation for each of these reactions:
a. 3-methyl-2-hexanol + CrO₃^-, H⁺ →
b. 1-pentanol + aqueous NaoH→
c. (CH₃)₂CHOH + Na→

Q4. Write equations for the best method to prepare each of the following ethers:
a. (CH₃)₂CHCH₂OCH₂CH₂CH₃
b. CH₃CH₂OCH₂CH₃

Q5. Give the structure of this product:
CH₂=OCCH₃ 1. → LialH₄ 2. → H₂O, H⁺

Q6. Complete the following equations:
a. CH₃CH₂=oCNHCH₂CH₃ → LialH₄
b. CH₃CH₂I⁺(CH₃)₂NH →