Organic Synthesis: Master the Art of Constructing Organic Compounds

Question 1

Which intermediate species is formed during an SN2 reaction mechanism?

Accepted Answer

Transition state

Answer

Carbocation

Answer

Carbanion

Answer

Free radical

Question 2

When protecting an amine functional group, which protecting group is commonly used?

Accepted Answer

Tosyl

Answer

Acetyl

Answer

Methoxy

Answer

Triethylamine

Question 3

Which factor does not influence the rate of an organic reaction?

Accepted Answer

Molecular shape

Answer

Temperature

Answer

Concentration of reactants

Answer

Nature of the solvent

Question 4

For the selective reduction of an alkyne to an alkene, which reagent can be employed?

Accepted Answer

Hydrogen gas over Lindlar's catalyst

Answer

Lithium aluminum hydride

Answer

Sodium borohydride

Answer

Potassium permanganate

Question 5

Which of the following is NOT a typical characteristic of a nucleophile?

Accepted Answer

Contains a hydrogen atom that can be abstracted

Answer

Ability to donate a lone pair of electrons

Answer

Negatively charged

Answer

Acts as a base

Question 6

The nucleophilic substitution reaction of an alkyl halide with hydroxide ion proceeds via which mechanism?

Accepted Answer

SN2 mechanism

Answer

SN1 mechanism

Answer

E1 mechanism

Answer

E2 mechanism

Question 7

Which of the following reagents is commonly employed for the dehydration of alcohols?

Accepted Answer

Concentrated sulfuric acid

Answer

Hydrochloric acid

Answer

Sodium hydroxide

Answer

Potassium dichromate

Question 8

The addition of an electrophile to an alkene results in the formation of which intermediate?

Accepted Answer

Carbocation

Answer

Alkyl halide

Answer

Alkoxide

Answer

Carbanion

Question 9

What is the major product of the Diels-Alder reaction?

Accepted Answer

Cyclohexadiene

Answer

Cyclohexene

Answer

Cyclohexane

Answer

Benzene

Question 10

In the reaction CH3Br + OH- → CH3OH, what species acts as the nucleophile?

Accepted Answer

OH-

Answer

CH3Br

Answer

CH3OH

Answer

Br-

Question 11

What is the expected product of the elimination reaction CH3CH2Br + KOH →?

Accepted Answer

CH2=CH2

Answer

CH3CH2OH

Answer

CH3CH=O

Answer

CH3CH2K

Question 12

In a Friedel-Crafts acylation reaction, what is the primary starting material?

Accepted Answer

Acyl chloride

Answer

Ketone

Answer

Alkyl halide

Answer

Aldehyde

Question 13

Which of the following is not considered a fundamental type of organic reaction?

Accepted Answer

Polymerization

Answer

Addition

Answer

Substitution

Answer

Elimination

Question 14

Which of the following reagents is commonly used to oxidize a primary alcohol to an aldehyde?

Accepted Answer

PCC

Answer

KMnO4

Answer

NaBH4

Answer

LiAlH4

Question 15

The following IR spectrum exhibits a strong peak at 1710 cm-1. What functional group is most likely present?

Accepted Answer

C=O

Answer

C-O

Answer

C-N

Answer

O-H

Question 16

Which of the following is the most efficient method for synthesizing a symmetrical alkane?

Accepted Answer

Wurtz reaction

Answer

Grignard reaction

Answer

Alkylation of an alkyl halide

Answer

Hydroboration-oxidation

Question 17

In the formation of alkenes from alkyl halides, which reaction mechanism is most commonly observed?

Accepted Answer

Elimination

Answer

Electrophilic addition

Answer

Nucleophilic substitution

Answer

Radical addition

Question 18

In the Williamson ether synthesis, what serves as the initial reactant?

Accepted Answer

Alcohol and alkyl halide

Answer

Alcohol and acid chloride

Answer

Aldehyde and alcohol

Answer

Ketone and amine

Question 19

Which reaction converts an aldehyde into an alcohol?

Accepted Answer

Reduction

Answer

Grignard reaction

Answer

Aldol condensation

Answer

Oxidation

Question 20

Which molecule exhibits chirality?

Accepted Answer

2-Butanol

Answer

Propane

Answer

Ethanol

Answer

Acetone

Question 21

Which of the following is NOT a key principle of organic synthesis?

Accepted Answer

Memorizing reaction products

Answer

Analyzing reaction mechanisms

Answer

Designing synthetic routes

Answer

Understanding functional group transformations

Question 22

In a nucleophilic substitution reaction, the species that attacks the electrophile is known as a:

Accepted Answer

Nucleophile

Answer

Electrophile

Answer

Free radical

Answer

Carboc Cation

Question 23

The Wittig reaction is primarily used to synthesize:

Accepted Answer

Alkenes

Answer

Alkynes

Answer

Alcohols

Answer

Ketones

Question 24

The Woodward-Hoffmann rules are primarily used to predict the:

Accepted Answer

Stereochemistry of concerted reactions

Answer

Reactivity of organic compounds

Answer

Stability of organic molecules

Answer

Mechanism of organic reactions

Question 25

Which type of reaction is commonly used to create a new carbon-carbon bond between two carbonyl compounds?

Accepted Answer

Aldol condensation

Answer

Michael addition

Answer

Suzuki-Miyaura coupling

Answer

Wittig reaction

Question 26

What is the mechanism of the Diels-Alder reaction?

Accepted Answer

Cycloaddition

Answer

Nucleophilic addition

Answer

Electrophilic addition

Answer

Free radical addition

Question 27

Which of the following compounds is considered an aromatic hydrocarbon?

Accepted Answer

Benzene

Answer

Cyclohexane

Answer

1-Butene

Answer

2-Methylpropane

Question 28

What is the major product of the following reaction: CH3CH2CH2Br + NaOH?

Accepted Answer

CH3CH2CH2OH

Answer

CH3CH=CH2

Answer

CH3CH2COOH

Answer

CH3CH2CONa

Question 29

Which type of reaction mechanism involves the breaking of a bond between two carbon atoms?

Accepted Answer

Homolytic fission

Answer

Nucleophilic substitution

Answer

Electrophilic addition

Answer

Heterolytic fission

Question 30

What is the major product of the following reaction: CH3CH2CH=CH2 + HBr?

Accepted Answer

CH3CH2CHBrCH3

Answer

CH3CH2CH2CH2Br

Answer

CH3CHBrCH=CH2

Answer

CH2=CHCH2CH2Br

Question 31

What is the IUPAC name of the following compound: CH3(CH2)4COOH?

Accepted Answer

Hexanoic acid

Answer

Pentanoic acid

Answer

Heptananoic acid

Answer

Octanoic acid

Question 32

Which of the following techniques can be used to separate organic compounds based on their polarity?

Accepted Answer

Chromatography

Answer

Distillation

Answer

Extraction

Answer

Recrystallization

Question 33

What is the role of a catalyst in an organic reaction?

Accepted Answer

To decrease the activation energy of the reaction

Answer

To increase the activation energy of the reaction

Answer

To change the products of the reaction

Answer

To prevent the reaction from occurring

Question 34

Which step in an SN2 reaction is the slowest and therefore rate-determining?

Accepted Answer

Attack of the nucleophile on the electrophile

Answer

Formation of the nucleophile

Answer

Formation of the electrophile

Answer

Departure of the leaving group

Question 35

Which of the following functional groups is protected by a Boc protecting group?

Accepted Answer

Amine

Answer

Alcohol

Answer

Carboxylic acid

Answer

Aldehyde

Question 36

What is the product of the nucleophilic substitution reaction between 1-bromopropane and sodium methoxide?

Accepted Answer

1-methoxypropane

Answer

Propene

Answer

1-propanol

Answer

2-bromopropane

Question 37

In a nucleophilic substitution reaction, the species that attacks the substrate with a lone pair of electrons is termed:

Accepted Answer

Nucleophile

Answer

Electrophile

Answer

Carbene

Answer

Free radical

Question 38

The Diels-Alder reaction involves a cycloaddition between:

Accepted Answer

A conjugated diene and a dienophile

Answer

An aldehyde and a ketone

Answer

An alkyne and a nucleophile

Answer

An alkene and an electrophile

Question 39

Which reagent can selectively oxidize a primary alcohol to an aldehyde?

Accepted Answer

Pyridinium Chlorochromate (PCC)

Answer

Lithium Aluminium Hydride (LAH)

Answer

Potassium Permanganate (KMnO4)

Answer

Sodium Borohydride (NaBH4)

Question 40

In the Williamson ether synthesis, an alkyl halide reacts with an alkoxide ion to form:

Accepted Answer

An ether

Answer

A ketone

Answer

An alcohol

Answer

An ester

Question 41

Retrosynthesis analysis involves:

Accepted Answer

Working backwards from the desired product to identify the starting materials and synthetic steps

Answer

Balancing chemical equations

Answer

Determining the rate of a reaction

Answer

Predicting the products of a reaction based on the starting materials

Question 42

Which reagents can be used to convert an alcohol to an alkene?

Accepted Answer

Concentrated sulfuric acid and heat

Answer

Potassium permanganate

Answer

Sodium hydroxide

Answer

Sodium ethoxide

Question 43

The reaction of an alkyl halide with a negatively charged species (nucleophile) is known as:

Accepted Answer

Nucleophilic substitution

Answer

Electrophilic substitution

Answer

Nucleophilic addition

Answer

Electrophilic addition

Question 44

Which of the following is the primary product of the electrophilic aromatic substitution reaction between benzene and chlorine in the presence of an iron catalyst?

Accepted Answer

Chlorobenzene

Answer

Dichlorobenzene

Answer

Trichlorobenzene

Answer

Benzene chloride

Question 45

The synthesis of aspirin involves the reaction between:

Accepted Answer

Salicylic acid and acetic anhydride

Answer

Acetic acid and phenol

Answer

Benzoic acid and ethanol

Question 46

The regioselectivity of an electrophilic addition reaction to an unsymmetrical alkene is predicted by:

Accepted Answer

Markovnikov's rule

Answer

Bredt's rule

Answer

Saytzeff's rule

Answer

Zaitsev's rule

Question 47

The synthesis of complex organic molecules often requires:

Accepted Answer

Multiple steps and the use of protecting groups

Answer

The use of only one protecting group

Answer

A single reaction step

Answer

No need for purification