© 2016 Pearson Education, Inc.General, Organic, and Biological Chemistry: Structures of Life, 5/e Karen C.. Give the IUPAC name for the following: Sample Problem 13.1 Naming Alcohols...
Trang 1© 2016 Pearson Education, Inc.
General, Organic, and Biological Chemistry: Structures of Life, 5/e
Karen C Timberlake
Solution
Step 1 Name the longest carbon chain attached to the —OH group by replacing the e in the corresponding alkane name with ol To name the alcohol, the e in alkane name pentane is replaced by
ol.
Step 2 Number the chain starting at the end nearer to the —OH group This carbon chain is numbered from right to left to give the position of the —OH group as carbon 2, which is shown as a
prefix in the name 2-pentanol
Give the IUPAC name for the following:
Sample Problem 13.1 Naming Alcohols
Trang 2Step 3 Give the location and name of each substituent relative to the —OH group.
Study Check 13.1
Give the IUPAC name for the following:
Answer
3-chloro-1-butanol
Continued
Sample Problem 13.1 Naming Alcohols
Trang 3© 2016 Pearson Education, Inc.
General, Organic, and Biological Chemistry: Structures of Life, 5/e
Karen C Timberlake
Solution
Step 1 Name an aromatic alcohol as a phenol The compound is a phenol because it contains an —OH group attached to a benzene ring.
Give the IUPAC and common names for the following:
Sample Problem 13.2 Naming Phenols
Trang 4Step 2 Number the chain starting at the end nearer to the —OH group For a phenol, the carbon atom attached to the —OH group is carbon 1.
Step 3 Give the location and name for each substituent relative to the —OH group For the common name, use the prefix ortho (o-).
Continued
Sample Problem 13.2 Naming Phenols
Trang 5© 2016 Pearson Education, Inc.
General, Organic, and Biological Chemistry: Structures of Life, 5/e
Karen C Timberlake
Study Check 13.2
Give the IUPAC and common names for the following:
Answer
4-methylphenol (p-methylphenol; p-cresol)
Continued
Sample Problem 13.2 Naming Phenols
Trang 6Step 1 Write the alkane name of the longer carbon chain
Step 2 Name the oxygen and smaller alkyl group as an alkoxy group
Step 3 Number the longer carbon chain from the end nearer the alkoxy group and give its location
Give the IUPAC name for the following:
CH3—CH2—O—CH2—CH2—CH2—CH3
Sample Problem 13.3 Naming Ethers
Trang 7© 2016 Pearson Education, Inc.
General, Organic, and Biological Chemistry: Structures of Life, 5/e
Karen C Timberlake
Study Check 13.3
What is the IUPAC name of methyl phenyl ether?
Answer
methoxybenzene
Continued
Sample Problem 13.3 Naming Ethers
Trang 8a. The carbon atom bonded to the —OH group is attached to one alkyl group, which makes this a primary (1°) alcohol
b. The carbon atom bonded to the —OH group is attached to three alkyl groups, which makes this a tertiary (3°) alcohol
Study Check 13.4
Classify the following alcohol as primary (1°), secondary (2°), or tertiary (3°):
Answer
secondary (2°)
Classify each of the following alcohols as primary (1°), secondary (2°), or tertiary (3°):
a. CH3—CH2—CH2—OH b.
Sample Problem 13.4 Classifying Alcohols
Trang 9© 2016 Pearson Education, Inc.
General, Organic, and Biological Chemistry: Structures of Life, 5/e
Karen C Timberlake
Draw the condensed structural formula for the major alkene produced by the dehydration of each of the following alcohols:
a.
b.
Sample Problem 13.5 Dehydration of Alcohols
Solution
a. The 1-butanol loses —OH from carbon 1 and H— from carbon 2 to form 1-butene This is the only possible product
CH3—CH2—CH CH2
b. For the dehydration of an asymmetrical alcohol, we use Saytzeff’s rule to remove —OH from carbon 2 and H— from carbon 3, which has the smaller number of H atoms The major product is 2-pentene
CH3—CH—CH—CH2 CH3
Study Check 13.5
What is the name of the alkene produced by the dehydration of cyclopentanol?
Answer
cyclopentene
Trang 10a. This is a secondary (2°) alcohol, which oxidizes to a ketone
b. This is a primary (1°) alcohol, which oxidizes to an aldehyde
Study Check 13.6
Draw the condensed structural formula for the product formed by the oxidation of 2-pentanol
Draw the condensed or line-angle structural formula for the aldehyde or ketone formed by the oxidation of each of the following:
Sample Problem 13.6 Oxidation of Alcohols
Trang 11© 2016 Pearson Education, Inc.
General, Organic, and Biological Chemistry: Structures of Life, 5/e
Karen C Timberlake
Answer
Continued
Sample Problem 13.6 Oxidation of Alcohols