Organic Chemistry Review

Organic Chemistry Review Next Review

Functional Groups of Molecules

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The functional group -CHO is called a:

A. Formyl group
B. Carboxyl group
C. Hydroxyl group
D. Acetyl group

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The compound with the formula HCHO is:

A. Formic acid
B. Formaldehyde
C. Acetaldehyde
D. Acetone

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The compound HCOOH is:

A. Formic acid
B. Acetic acid
C. Formaldehyde
D. Acetaldehyde

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The functional group -COCH₃ is called a:

A. Formyl group
B. Carboxyl group
C. Acetyl group
D. Benzyl group

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The compound CH₃CHO is:

A. Formaldehyde
B. Acetic acid
C. Acetone
D. Acetaldehyde

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The compound CH₃COOH is:

A. Formic acid
B. Acetic acid
C. Acetaldehyde
D. Acetone

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The compound CH₃COCH₃ is:

A. Acetaldehyde
B. Acetic acid
C. Acetone
D. Acetylacetone

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The compound CH₃COCH₂COCH₃ is:

A. Acetone
B. Acetophenone
C. Acetaldehyde
D. Acetylacetone

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The compound C₆H₅COCH₃ is:

A. Acetophenone
B. Benzaldehyde
C. Benzoin
D. Benzoic acid

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The functional group -CH₂C₆H₅ is called a:

A. Acetyl group
B. Benzyl group
C. Phenyl group
D. Acryl group

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The compound C₆H₅CHO is:

A. Acetophenone
B. Benzoic acid
C. Benzaldehyde
D. Benzoin

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The compound C₆H₅COOH is:

A. Benzaldehyde
B. Benzoic acid
C. Acetophenone
D. Benzoin

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The compound C₆H₅CHOHCOC₆H₅ is:

A. Benzaldehyde
B. Benzoic acid
C. Acetophenone
D. Benzoin

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The compound C₆H₅CH=CH₂ is:

A. Styrene
B. Formene
C. Toluene
D. Phenol

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The functional group CH₂=CHCO- is called a:

A. Acetyl group
B. Acyl group
C. Acryl group
D. Formyl group

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The compound CH₂=CHCHO is:

A. Acetaldehyde
B. Acetin
C. Acrylic acid
D. Acrolein

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The compound CH₂=CHCOOH is:

A. Acrolein
B. Formic acid
C. Acrylic acid
D. Acetic acid

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The ion -COO⁻ is called a:

A. Carbonate ion
B. Carboxylate ion
C. Hydroxide ion
D. Bicarbonate ion

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The ion CO₃²⁻ is called a:

A. Carbonate ion
B. Carboxylate ion
C. Bicarbonate ion
D. Sulfate ion

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The compound H₂CO₃ is:

A. Formic acid
B. Acetic acid
C. Carbonic acid
D. Benzoic acid

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Which of the following describes alkanes?

A. All carbon–carbon bonds are single bonds
B. There is at least one double bond
C. There is at least one triple bond
D. There is at least one –OH group

Nomenclature

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When naming alkanes, which two components are used?

A. Number of hydrogens + suffix –ane
B. Number of carbons + suffix –ane
C. Number of carbons + suffix –ene
D. Number of hydrogens + suffix –ene

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What kind of bond do alkenes have, and which suffix is used for their name?

A. Single, –ane
B. Double, –ene
C. Triple, –yne
D. Double, –ane

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What kind of bond do alkynes have, and which suffix is used for their name?

A. Single, –ane
B. Double, –ene
C. Triple, –yne
D. Triple, –ane

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What functional group do alcohols contain, and which suffix or prefix is used in their nomenclature?

A. Ketone, –one, keto–
B. –OH, –ol, hydroxy–
C. –NH₂, –amine, amino–
D. Carbonyl, –al, formyl–

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What does the term "diol" imply about the molecule's functional groups?

A. It contains two carbonyl groups
B. It contains two hydroxyl groups
C. It contains two amino groups
D. It contains two alkyl groups

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What is the correct name for the simplest alkane (one carbon)?

A. Ethane
B. Methane
C. Propane
D. Butane

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What is the correct name for the alkane with three carbons?

A. Propane
B. Butane
C. Pentane
D. Ethane

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What is the correct name for the alkane with four carbons?

A. Pentane
B. Butane
C. Hexane
D. Propane

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What is the correct name for the alkane with five carbons?

A. Pentane
B. Hexane
C. Butane
D. Heptane

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What is the correct name for the alkane with six carbons?

A. Hexane
B. Pentane
C. Heptane
D. Octane

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What is the name of the functional group characterized by a carbon double‑bonded to oxygen?

A. Ether
B. Carbonyl
C. Hydroxyl
D. Amide

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On which carbon does the carbonyl group reside in an aldehyde?

A. Non‑terminal
B. Terminal
C. Middle
D. Any

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On which carbon does the carbonyl group reside in a ketone?

A. Terminal
B. Non‑terminal
C. The first carbon
D. The last carbon

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How is an alcohol classified as primary (1º), secondary (2º), or tertiary (3º)?

A. By how many carbons are attached to the hydroxyl group
B. By how many carbons are attached to the carbon bearing the hydroxyl group
C. By how many carbons are adjacent to the hydroxyl carbon
D. By how many carbons are at the end

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How is an amine classified as primary (1º), secondary (2º), or tertiary (3º)?

A. By how many carbons are attached to the nitrogen atom
B. By how many carbons are attached to the carbon bearing the amine
C. By how many carbons are adjacent to that carbon
D. By how many hydrogens

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Which functional group has the highest naming priority in organic nomenclature?

A. Alcohol
B. Ketone
C. Aldehyde
D. Carboxylic acid

Isomerism

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Which of the following best defines isomers?

A. They have different chemical formulas and the same arrangement of atoms
B. They have the same chemical formula but differ in stereochemical arrangement of atoms
C. They have totally different atoms but similar connectivity
D. They have the same stereochemical arrangement but different molecular formula

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Which type of isomers have identical chemical formulas but differ in the connectivity (structure) of their atoms?

A. Stereoisomers
B. Conformational isomers
C. Constitutional (structural) isomers
D. Geometric isomers

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Which term describes isomers that have the same connectivity but differ in their three‑dimensional arrangement?
stereo

A. Constitutional isomers
B. Conformational isomers
C. Stereoisomers
D. Positional isomers

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When four different groups are attached to a central carbon, that carbon is called a(n):

A. Achiral center
B. Stereogenic center
C. Chiral center
D. Meso center

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If a molecule has "n" chiral (asymmetric) carbons (and no symmetry that reduces possibilities), how many possible stereoisomers are predicted?

A. n
B. 2ⁿ
C. 2n
D. n²

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Which kind of isomers differ by rotation around a single σ (sigma) bond?

A. Constitutional isomers
B. Stereoisomers (configurational)
C. Conformational isomers
D. Geometric isomers

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A certain Newman projection is described as "anti." Which of the following best matches that description?

A. Substituents are eclipsed (0° apart)
B. Substituents are 60° apart
C. Substituents are 120° apart
D. Substituents are 180° apart

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A Newman projection is described as "gauche." What is the dihedral angle between substituents in that conformation?

A. 0°
B. 60°
C. 120°
D. 180°

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When a Newman projection is called "eclipsed," what characterizes that conformation?

A. Substituents on adjacent carbons are staggered
B. Substituents align, creating maximum torsional strain
C. It is the lowest energy conformation
D. Substituents are anti to each other

Chemical Bonding

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In a cyclohexane ring, an equatorial bond is one that is:

A. Perpendicular to the ring's axis
B. Parallel to the ring's axis
C. In the same plane as the ring
D. Part of a double bond

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In contrast, an axial bond in a cyclohexane ring is one that is:

A. Perpendicular to the ring's axis
B. Parallel to the ring's axis
C. In the same plane as the ring
D. Part of a substituent in the ring plane

Reaction Mechanisms

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What is chemoselectivity?

A. The ability of a reagent or intermediate to react with one group or atom in a molecule in preference to another group or atom present in the same molecule
B. The ability of a reagent to react with all groups or atoms in a molecule equally
C. The ability of a reagent to react with only one specific molecule
D. The ability of a reagent to react with multiple molecules simultaneously

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A nucleophile:

A. Contains lone pairs of electrons or pi bonds and is "nucleus-loving"
B. Contains no lone pairs of electrons and is "electron-loving"
C. Contains lone pairs of electrons and is "electron-hating"
D. Contains pi bonds and is "nucleus-hating"

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Nucleophilicity is a term used to describe:

A. The strength of a nucleophile
B. The strength of an electrophile
C. The strength of a leaving group
D. The strength of a solvent

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Electrophiles:

A. Are electron-loving
B. Are electron-hating
C. Contain a negative charge or are negatively polarized
D. Contain a positive charge or are positively polarized

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Leaving groups:

A. Are molecular fragments that retain the electrons after heterolysis
B. Are molecular fragments that donate electrons after heterolysis
C. Are molecular fragments that retain protons after heterolysis
D. Are molecular fragments that donate protons after heterolysis

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Cl⁻ and Br⁻ are:

A. Good leaving groups
B. Bad leaving groups
C. Neutral leaving groups
D. Good nucleophiles

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-OH is a:

A. Good leaving group
B. Bad leaving group
C. Neutral leaving group
D. Non-leaving group

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The "SN" in SN1 and SN2 reactions refers to:

A. Substitution Nucleophilic
B. Substitution Nuclear
C. Sequential Nucleophilic
D. Single Nucleophilic

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The number 1 in an SN1 reaction refers to the fact that the reaction is:

A. Unimolecular
B. Bimolecular
C. One-step
D. Uninuclear

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An SN1 reaction has:

A. One step
B. Two steps
C. Three steps
D. Four steps

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An SN2 reaction has:

A. One step
B. Two steps
C. Three steps
D. Four steps

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SN1 products are:

A. A racemic mixture
B. Optically active
C. Optically inactive
D. A single enantiomer

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SN2 reactions lead to:

A. Retention of stereochemistry
B. Inversion of stereochemistry
C. Racemization
D. No change in stereochemistry

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Which type of substrate favors an SN1 reaction?

A) Methyl
B) Primary
C) Secondary
D) Tertiary

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In an SN1 reaction, the rate-determining step involves:

A. Formation of a carbanion
B. Leaving group departure
C. Formation of a carbocation
D. Proton abstraction

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Which solvent type stabilizes the carbocation intermediate in an SN1 reaction?
solvent types

A. Polar aprotic
B. Nonpolar
C. Polar protic
D. Aprotic

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What is the stereochemical outcome of an SN1 reaction?

A. Inversion of configuration
B. Retention of configuration
C. Racemization
D. No change in configuration

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Which type of substrate MOST readily favors an SN2 reaction?

A. Methyl
B. Primary
C. Secondary
D. Tertiary

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In an SN2 reaction, the nucleophile attacks the substrate:

A. After the leaving group departs
B. Simultaneously as the leaving group departs
C. Before the leaving group departs
D. Only in the presence of a catalyst

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Which solvent type favors an SN2 reaction?

A. Polar protic
B. Nonpolar
C. Polar aprotic
D. Aprotic

Check Your Progress

Elimination Reactions

A strong base is typically associated with which elimination mechanism?

A. E1
B. E2
C. Both E1 and E2
D. Neither E1 nor E2

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Which type of substrate favors an E2 elimination reaction?

A. Methyl
B. Primary
C. Secondary
D. Tertiary

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In an E2 reaction, the base abstracts a proton:

A. Before the leaving group departs
B. Simultaneously as the leaving group departs
C. After the leaving group departs
D. Only in the presence of a catalyst

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Which elimination mechanism involves the formation of a carbocation intermediate?

A. E1
B. E2
C. Both E1 and E2
D. Neither E1 nor E2

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A tertiary substrate with a polar protic solvent will favor which reaction mechanism?

A. SN1
B. SN2
C. E1
D. E2

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Which of the following is a characteristic of polar protic solvents?

A. They do not participate in hydrogen bonding
B. They can solvate anions effectively
C. They are typically aprotic
D. They are nonpolar

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Which of the following is a polar protic solvent?

A. Acetone
B. DMSO
C. Water
D. DMF

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Which of the following is a polar aprotic solvent?

A. Acetone
B. Methanol
C. Water
D. Ethanol

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A secondary substrate with a polar protic solvent will favor which reaction mechanism?

A. SN1
B. SN2
C. E1
D. E2

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A secondary substrate with a polar aprotic solvent will favor which reaction mechanism?

A. SN1
B. SN2
C. E1
D. E2

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Which of the following bases is considered a strong base?

A. Water
B. Methanol
C. Sodium hydroxide
D. Acetic acid

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Which of the following bases is considered a weak base?

A. Sodium hydroxide
B. Potassium tert-butoxide
C. Water
D. Ammonia

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Which of the following substrates cannot undergo an elimination reaction?

A. Methyl
B. Primary
C. Secondary
D. Tertiary

Alcohols

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What suffix or prefix is used to name alcohols?

A. –ene
B. –ol or hydroxy-
C. –ane
D. –yne

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How are 1º, 2º, and 3º alcohols named?

A. According to the number of hydrogen atoms attached to the hydroxyl group
B. According to the number of carbons attached to the carbon bearing the hydroxyl group
C. According to the number of oxygen atoms in the molecule
D. According to the number of bonds in the carbon chain

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Which of the following is a primary alcohol?

A. CH₃CH₂OH
B. CH₃CHOHCH₃
C. (CH₃)₃COH
D. C₆H₅OH

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Which of the following is a secondary alcohol?

A. CH₃CH₂OH
B. CH₃CHOHCH₃
C. (CH₃)₃COH
D. C₆H₅OH

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Which of the following is a tertiary alcohol?

A. CH₃CH₂OH
B. CH₃CHOHCH₃
C. (CH₃)₃COH
D. C₆H₅OH

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What is the compound known as when a hydroxyl group is attached to a benzene ring?

A. Alcohol
B. Phenol
C. Ether
D. Ketone

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What is the position of substituents on a benzene ring when they are in the ortho position?

A. Adjacent carbons
B. One carbon apart
C. Opposite sides of the ring
D. Attached to a hydroxyl group

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What is the position of substituents on a benzene ring when they are in the meta position?

A. Adjacent carbons
B. One carbon apart
C. Opposite sides of the ring
D. Attached to a hydroxyl group

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What are quinones?

A. Aromatic compounds with hydroxyl groups
B. Conjugated cyclic diketones that are not aromatic
C. Alcohols with two hydroxyl groups
D. Compounds with a hydroxyl group attached to a carbonyl group

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What are hydroxyquinones?

A. Compounds produced by oxidation of quinones
B. Compounds produced by reduction of quinones
C. Compounds with two hydroxyl groups attached to a benzene ring
D. Compounds with a hydroxyl group attached to a carbonyl group

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What is ubiquinone?

A. A biologically active quinone that acts as an electron acceptor in the electron transport chain
B. A compound produced by oxidation of quinones
C. A type of alcohol with a hydroxyl group attached to a benzene ring
D. A conjugated cyclic diketone that is aromatic

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When an alcohol is oxidized, it can become which of the following compounds?

A. Aldehyde, ketone, or carboxylic acid
B. Alkene, alkane, or alkyne
C. Ether, ester, or amide
D. Phenol, quinone, or hydroxyquinone

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Treatment of a primary alcohol with pyridinium chlorochromate (PCC) leads to the formation of a/an:

A. Carboxylic acid
B. Ketone
C. Aldehyde
D. Ester

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Alcohols can be converted to what two groups to make them better leaving groups for nucleophilic substitution reactions?

A. Esters or ethers
B. Aldehydes or ketones
C. Carboxylic acids or amines
D. Mesylates or tosylates

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Aldehydes and ketones can be protected from reaction by converting them into:

A. Ethers or esters
B. Acetals or ketals
C. Alcohols or phenols
D. Carboxylic acids or amides

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A primary carbon with two —OR groups and a hydrogen atom is characteristic of a/an:

A. Hemiacetal
B. Hemiketal
C. Acetal
D. Ketal

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A secondary carbon with two —OR groups is characteristic of a/an:

A. Hemiacetal
B. Hemiketal
C. Acetal
D. Ketal

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Amino acids are simple organic compounds containing both a/an … group and a/an … group:

A. Hydroxyl (—OH) and aldehyde (—CHO)
B. Carboxyl (—COOH) and amino (—NH₂)
C. Ketone (—C(O)—) and sulfhydryl (—SH)
D. Amide (—C(O)NH₂) and phosphate (—OPO₃²⁻) group