Question 1

What is the IUPAC name of the following compound?

Accepted Answer

A)  1,1-dimethyl-3-pentanone 
B)  3,3-methyl-1-pentanone 
C)  3,3-dimethylcyclopentanone 
D)  1,1-dimethyl-3-cyclopentanone 
A)  1,1-dimethyl-3-pentanone 
B)  3,3-methyl-1-pentanone 
C)  3,3-dimethylcyclopentanone 
D)  1,1-dimethyl-3-cyclopentanone C

Question 2

Which of the following functional groups contain carbonyl groups?

Accepted Answer

A)  carboxylic acids 
B)  esters 
C)  aldehydes 
D)  all of these 
A)  carboxylic acids 
B)  esters 
C)  aldehydes 
D)  all of these D

Question 3

Which of the following has intermolecular hydrogen bonds?

Accepted Answer

A)  pure acetone 
B)  pure formaldehyde 
C)  a mixture of acetone and formaldehyde 
D)  none of these 
A)  pure acetone 
B)  pure formaldehyde 
C)  a mixture of acetone and formaldehyde 
D)  none of these D

Question 4

Answer the following question based on the given ball-and-stick model. Atoms other than carbon and hydrogen are labeled with the symbol of the element.   Which of the following statements is true of the given compound?

Accepted Answer

A)  It participates in hydrogen bonding with water. 
B)  It has a tetrahedral geometry at the carbonyl carbon. 
C)  It has a higher boiling point than the corresponding acid. 
D)  All of these statements are true. 
A)  It participates in hydrogen bonding with water. 
B)  It has a tetrahedral geometry at the carbonyl carbon. 
C)  It has a higher boiling point than the corresponding acid. 
D)  All of these statements are true.

Question 5

Which of the following compounds has the highest water solubility?

Accepted Answer

A)  butanal 
B)  1-butanol 
C)  1-hexanol 
D)  hexanal 
A)  butanal 
B)  1-butanol 
C)  1-hexanol 
D)  hexanal

Question 6

What is the IUPAC name of the following compound?

Accepted Answer

A)  4-hexanone 
B)  3-hexanone 
C)  ethyl propyl ketone 
D)  propyl ethyl ketone 
A)  4-hexanone 
B)  3-hexanone 
C)  ethyl propyl ketone 
D)  propyl ethyl ketone

Question 7

Which of the following statements is true of aldehydes and ketones?

Accepted Answer

A)  Both aldehydes and ketones are easily oxidized. 
B)  Neither aldehydes nor ketones are easily oxidized. 
C)  Aldehydes are easily oxidized, but ketones cannot be readily oxidized. 
D)  Ketones are easily oxidized, but aldehydes cannot be readily oxidized. 
A)  Both aldehydes and ketones are easily oxidized. 
B)  Neither aldehydes nor ketones are easily oxidized. 
C)  Aldehydes are easily oxidized, but ketones cannot be readily oxidized. 
D)  Ketones are easily oxidized, but aldehydes cannot be readily oxidized.

Question 8

If pairs of enantiomers are only counted once, how many different aldehydes have the molecular formula C5H10O?

Accepted Answer

A)  2 
B)  3 
C)  4 
D)  5 
A)  2 
B)  3 
C)  4 
D)  5

Question 9

Which types of biologically important molecules include many cyclic hemiacetals?

Accepted Answer

A)  carbohydrates 
B)  lipids 
C)  proteins 
D)  none of these 
A)  carbohydrates 
B)  lipids 
C)  proteins 
D)  none of these

Question 10

Which structural feature is common to aldehydes and ketones?

Accepted Answer

A)  an oxygen atom bonded to both a carbon atom and a hydrogen atom 
B)  an oxygen atom bonded to two carbon atoms 
C)  an oxygen atom double bonded to a carbon atom 
D)  two oxygen atoms bonded to the same carbon atom 
A)  an oxygen atom bonded to both a carbon atom and a hydrogen atom 
B)  an oxygen atom bonded to two carbon atoms 
C)  an oxygen atom double bonded to a carbon atom 
D)  two oxygen atoms bonded to the same carbon atom

Question 11

Which of the following statements is correct regarding the reduction of an unsaturated aldehyde or ketone using H2 in the presence of a transition metal catalyst?

Accepted Answer

A)  Both the carbon-carbon and the carbon-oxygen double bonds are reduced at the same rate. 
B)  The carbon-carbon double bond is reduced more rapidly than the carbon-oxygen double bond. 
C)  The carbon-oxygen double bond is reduced more rapidly than the carbon-carbon double bond. 
D)  Unsaturated aldehydes and ketones do not undergo any reduction reactions under these conditions. 
A)  Both the carbon-carbon and the carbon-oxygen double bonds are reduced at the same rate. 
B)  The carbon-carbon double bond is reduced more rapidly than the carbon-oxygen double bond. 
C)  The carbon-oxygen double bond is reduced more rapidly than the carbon-carbon double bond. 
D)  Unsaturated aldehydes and ketones do not undergo any reduction reactions under these conditions.

Question 12

What is the IUPAC name of the following compound?

Accepted Answer

A)  2,4-dimethyl-6-hexanal 
B)  2-aldehydomethyl-4-methylpentane 
C)  3,5-dimethyl-2-hexanal 
D)  3,5-dimethylhexanal 
A)  2,4-dimethyl-6-hexanal 
B)  2-aldehydomethyl-4-methylpentane 
C)  3,5-dimethyl-2-hexanal 
D)  3,5-dimethylhexanal

Question 13

Which of the following is true of hemiacetals?

Accepted Answer

A)  The most stable hemiacetals are noncyclic. 
B)  Hemiacetals react with alcohols to form acetates. 
C)  Hemiacetals react with alcohols to form acetals. 
D)  Hemiacetals contain two carbonyl groups in their stable form. 
A)  The most stable hemiacetals are noncyclic. 
B)  Hemiacetals react with alcohols to form acetates. 
C)  Hemiacetals react with alcohols to form acetals. 
D)  Hemiacetals contain two carbonyl groups in their stable form.

Question 14

Which of the following is the first step in the acid catalyzed formation of an acetal?

Accepted Answer

A)  A proton is added to the carbonyl oxygen, giving a resonance-stabilized cation. 
B)  An electrophile and a nucleophile react to form a new covalent bond. 
C)  A proton is transferred from one oxygen to another oxygen. 
D)  A tertiary carbocation is formed by breaking the bond between a hydroxyl group and a carbon. 
A)  A proton is added to the carbonyl oxygen, giving a resonance-stabilized cation. 
B)  An electrophile and a nucleophile react to form a new covalent bond. 
C)  A proton is transferred from one oxygen to another oxygen. 
D)  A tertiary carbocation is formed by breaking the bond between a hydroxyl group and a carbon.

Question 15

Which of the following is the least soluble in water?

Accepted Answer

A)  2-butanone 
B)  1-hydroxy-2-butanone 
C)  2,3-dihydroxybutanal 
D)  2-pentanone 
A)  2-butanone 
B)  1-hydroxy-2-butanone 
C)  2,3-dihydroxybutanal 
D)  2-pentanone

Question 16

Which of the following compounds can undergo keto-enol tautomerism?

Accepted Answer

A)  2,4-dimethyl-3-pentanone 
B)  2,2,4,4-tetramethyl-3-pentanone 
C)  both 2,4-dimethyl-3-pentanone and 2,2,4,4-tetramethyl-3-pentanone 
D)  none of these 
A)  2,4-dimethyl-3-pentanone 
B)  2,2,4,4-tetramethyl-3-pentanone 
C)  both 2,4-dimethyl-3-pentanone and 2,2,4,4-tetramethyl-3-pentanone 
D)  none of these

Question 17

Which of the following compounds has the lowest boiling point?

Accepted Answer

A)  2-butanone 
B)  2-heptanone 
C)  2-hexanone 
D)  2-pentanone 
A)  2-butanone 
B)  2-heptanone 
C)  2-hexanone 
D)  2-pentanone

Question 18

How many ketone functional groups are present in the following compound?

Accepted Answer

A)  2 
B)  1 
C)  4 
D)  5 
A)  2 
B)  1 
C)  4 
D)  5

Question 19

What is the IUPAC name of the following compound?

Accepted Answer

A)  2,3-dihydroxycyclopentanone 
B)  1,2-dihydroxy-3-cyclopentanone 
C)  cyclopentanone-1,2-diol 
D)  cyclopentanone-2,3-diol 
A)  2,3-dihydroxycyclopentanone 
B)  1,2-dihydroxy-3-cyclopentanone 
C)  cyclopentanone-1,2-diol 
D)  cyclopentanone-2,3-diol

Question 20

What is the final product obtained when 2-hexanone is treated with potassium dichromate in the presence of sulfuric acid?

Accepted Answer

A)  an equilibrium mixture of 2-hexanone and hemiacetal 
B)  hexanol 
C)  hexanoic acid 
D)  none of these, as 2-hexanone does not undergo oxidation readily 
A)  an equilibrium mixture of 2-hexanone and hemiacetal 
B)  hexanol 
C)  hexanoic acid 
D)  none of these, as 2-hexanone does not undergo oxidation readily

Exam 16: Aldehydes and Ketones

What is the IUPAC name of the following compound?

Which of the following functional groups contain carbonyl groups?

Which of the following has intermolecular hydrogen bonds?

Answer the following question based on the given ball-and-stick model. Atoms other than carbon and hydrogen are labeled with the symbol of the element. Which of the following statements is true of the given compound?

Which of the following compounds has the highest water solubility?

What is the IUPAC name of the following compound?

Which of the following statements is true of aldehydes and ketones?

If pairs of enantiomers are only counted once, how many different aldehydes have the molecular formula C5H10O?

Which types of biologically important molecules include many cyclic hemiacetals?

Which structural feature is common to aldehydes and ketones?

Which of the following statements is correct regarding the reduction of an unsaturated aldehyde or ketone using H2 in the presence of a transition metal catalyst?

What is the IUPAC name of the following compound?

Which of the following is true of hemiacetals?

Which of the following is the first step in the acid catalyzed formation of an acetal?

Which of the following is the least soluble in water?

Which of the following compounds can undergo keto-enol tautomerism?

Which of the following compounds has the lowest boiling point?

How many ketone functional groups are present in the following compound?

What is the IUPAC name of the following compound?

What is the final product obtained when 2-hexanone is treated with potassium dichromate in the presence of sulfuric acid?

Matter, Energy, and Measurement

Atoms

Chemical Bonds

Chemical Reactions

Gases, Liquids, and Solids

Solutions and Colloids

Reaction Rates and Chemical Equilibrium

Acids and Bases

Nuclear Chemistry

Organic Chemistry

Alkanes

Alkenes, Alkynes, and Aromatic Compounds

Alcohols, Ethers, and Thiols

Chirality: the Handedness of Molecules

Amines

Carboxylic Acids

Carboxylic Anhydrides, Esters, and Amides

Carbohydrates

Lipids

Proteins

Enzymes

Chemical Communications: Neurotransmitters and Hormones

Nucleotides, Nucleic Acids, and Heredity

Gene Expression and Protein Synthesis

Bioenergetics: How the Body Converts Food to Energy

Specific Catabolic Pathways: Carbohydrate, Lipid, and Protein Metabolism

Biosynthetic Pathways

Nutrition

Immunochemistry

Body Fluids

Filters

If pairs of enantiomers are only counted once, how many different aldehydes have the molecular formula C₅H₁₀O?

Which of the following statements is correct regarding the reduction of an unsaturated aldehyde or ketone using H₂ in the presence of a transition metal catalyst?