Textbook Question
Arrange the following 6-carbon compounds in order of their expected boiling points, and explain your ranking:
a. Hexane
b. 1-Hexanol
c. Dipropyl ether (CH3CH2CH2—O—CH2CH2CH3)
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14. Compounds with Oxygen or Sulfur
Naming Ethers
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Provide the name for the following ether.
A
tert-butyl pentyl ether
B
sec-butyl pentyl ether
C
sec-butyl pentanoate
D
pentyl sec-butyl ether
Verified step by step guidance1
Identify the longest carbon chain on either side of the oxygen atom in the ether structure. In this case, there is a five-carbon chain (pentyl group) and a four-carbon chain with a branching (butyl group).
Determine the type of butyl group present. The four-carbon chain is attached to the oxygen at the second carbon, making it a sec-butyl group.
Name the ether by listing the alkyl groups in alphabetical order followed by the word 'ether'. Here, 'pentyl' comes before 'sec-butyl' alphabetically.
Combine the names of the alkyl groups with 'ether' to form the complete name: 'pentyl sec-butyl ether'.
Verify the structure matches the name by ensuring the correct number of carbons and the correct branching are represented in the name.
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