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Problem 15.1
Which of the following molecules contain aldehyde or ketone functional groups? You may want to refer to Table 15.1, Table 12.1, and Figure 15.3 to help in your identification. Copy the formulas and circle these functional groups.
a. <IMAGE> Prostaglandin E₁
b. <IMAGE> Testosterone (a male hormone)
c. <IMAGE> Vanillin (a flavoring agent)
d. C₄H₉COCH₃
e. C₄H₉CHO
Problem 15.12
What ketones or aldehydes might be reduced to yield the following alcohols?
a. <IMAGE>
b. <IMAGE>
c. HOCH2―CH2―CH2OH
Problem 15.14
Determine whether the following compounds are acetals or ketals. Draw the structure of the aldehyde or ketone it came from.
c.<IMAGE>
Problem 15.15
Draw the structures of the hemiacetals or hemiketals formed in these reactions:
b. <IMAGE>
Problem 15.20a
The carbonyl group can be reduced by addition of a hydride ion (H⁻) and (H⁺) a proton
. Removal of H⁻ and H⁺ from an alcohol results in a carbonyl group <IMAGE>
a.To which atom of the carbonyl is the hydride ion added and why?
Problem 15.20b
The carbonyl group can be reduced by addition of a hydride ion (H⁻) and (H⁺) a proton
. Removal of H⁻ and H⁺ from an alcohol results in a carbonyl group <IMAGE>
b. In the reaction, indicate which direction represents reduction and which represents oxidation.
Problem 15.21
A fundamental difference between aldehydes and ketones is that one can be oxidized to carboxylic acids but the other cannot. Which is which? Give an example of a test to differentiate aldehydes from ketones.
Problem 15.26a
Draw a structure for a compound that meets each of the following descriptions:
A 6-carbon cyclic ketone with a methyl group on the beta carbon
Problem 15.26b
Draw a structure for a compound that meets each of the following descriptions:
An aldehyde with four carbons
Problem 15.26c
Draw a structure for a compound that meets each of the following descriptions:
An alpha-bromoaldehyde, C₄H₇BrO
Problem 15.27b
Draw a structure for a compound that meets each of the following descriptions:
An 8-carbon ketone with six carbons as its longest chain
Problem 15.27d
Draw a structure for a compound that meets each of the following descriptions:
A cyclic alpha-hydroxyketone, C₅H₈O₂
Problem 15.28a
Indicate which compounds contain aldehyde or ketone carbonyl groups.
<IMAGE>
Problem 15.28c
Indicate which compounds contain aldehyde or ketone carbonyl groups.
CH3CH2―O―CH2―CHO
Problem 15.28f
Indicate which compounds contain aldehyde or ketone carbonyl groups.
<IMAGE>
Problem 15.29c
Redraw each of the following in line structure format. Indicate which compounds have an aldehyde carbonyl group, a ketone carbonyl group, or neither.
<IMAGE>
Problem 15.29e
Redraw each of the following in line structure format. Indicate which compounds have an aldehyde carbonyl group, a ketone carbonyl group, or neither.
e. CH3CH2COCH2CH3
Problem 15.3
Draw structures corresponding to the following names:
a.Octanal
b.Methyl phenyl ketone
c.4-Methylhexanal
d.Methyl tert-butyl ketone
Problem 15.30a
Draw structures corresponding to the following aldehyde and ketone names:
3-Methylpentanal
Problem 15.31b
Draw structures corresponding to the following aldehyde and ketone names:
4-Ethyl-2-isopropylhexanal
Problem 15.31e
Draw structures corresponding to the following aldehyde and ketone names:
1,1,1-Trichloro-3-pentanone
Problem 15.32a
Give systematic names for the following aldehydes and ketones:
<IMAGE>
Problem 15.33b
Give IUPAC names for the following aldehydes and ketones: <IMAGE>
Problem 15.34a
The following names are incorrect. What is wrong with each?
1-Pentanone
Problem 15.35b
The following names are incorrect. What is wrong with each?
2-Butanal
Problem 15.38
Which of the following compounds will react with Tollens' reagent? With Benedict's reagent?
a. Cyclopentanon
b. Hexanal
c. <IMAGE>
Problem 15.39a
Draw the structures of the products formed when the following compounds react with a reducing agent.
<IMAGE>
Problem 15.4
Give systematic, IUPAC names for the following compounds. Redraw each in line structure format.
O
II
a. CH₃CH₂CH₂CH₂
O
II
b. CH₃CH₂CCH₂CH₃
CH₃ O
I II
c. CH₃CH₂CHCH₂CH
d. Dipropyl ketone
Problem 15.43a
Write the structures of the hemiacetal or hemiketal that result from reactions (a) and (b). Write the structures of the complete hydrolysis products of the acetal or ketal in (c) and (d).
Acetone + Ethanol → ?
Problem 15.44
Cyclic hemiacetals commonly form if a molecule has both an alcohol group and a carbonyl group elsewhere in the same molecule, especially if they are four or five carbons apart. What is the structure of the hydroxy aldehyde from which this hemiacetal might form?
<IMAGE> Cyclic hemiacetal
