Propose a synthesis plan for the following compound. You can use any alkenes or cycloalkenes that contain no more than six carbon atoms as the starting material.

Show how to accomplish each of the transformations shown below.

Draw chemical structures corresponding to the following IUPAC names:

a. (S)-4-chloropent-4-en-2-ol
b. cis-cyclobutan-1,2-diol

For each pair of compounds, determine which compound boils at a higher temperature. Give a brief explanation for your predictions.
(i) heptan-1-ol or 3,3-dimethylpentan-1-ol
(ii) pentan-2-one or pentan-2-ol

Determine the IUPAC name of the following alcohols and classify them as either primary (1°), secondary (2°), or tertiary alcohol (3°).

Illustrate the condensed and skeletal structures of isobutyl isopropyl ether.

Give an IUPAC and a common name for each of the following compounds.
a. CH₃CH₂OCH=CHCH₃
b. BrCH₂CH₂CH₂OCH₂CH₃
c. CH₃OCH(CH₃)₂ 

Draw the structures of the ethers given below.
a. vinyl ethyl ether
b. cyclopentene oxide
c. diallyl ether

Draw the structure consistent with the name 2,3-diethyl-2,3-dimethyloxirane.

Draw the structure consistent with the name 3,4-epoxy-2-methylheptane.

What are two possible systematic names for the following?

(i)

(ii)

Give the IUPAC name of the following acyclic thiol. 

What is the corresponding structure of a compound with the IUPAC name (R)-3,3-dimethyl-1-phenylpentane-1-thiol?