Deck 27: Reactions of Organic Compounds

Question 1

Synthesis of alkanes from alkyl halides is a typical example of E2 reaction.

Answer 1

False

Question 2

Electrophilic substitution reactions are typical reactions of aromatic compounds.

Answer 2

True

Question 3

Find the combination of conditions that are the best for S_N2 reactions.

A)The substrate is a tertiary alkyl iodide,solvent is aprotic,polar and the nucleophile is a strong base.
B)The substrate is a primary alkyl iodide,solvent is aprotic,polar and the nucleophile is a strong base.
C)The substrate is a primary alkyl fluoride,solvent is protic,polar and the nucleophile is a strong base.
D)The substrate is a primary alkyl iodide,solvent is non-polar and the nucleophile is a weak base.
E)The substrate is a tertiary alkyl iodide,solvent is non-polar and the nucleophile is a strong base.

Answer 3

The substrate is a primary alkyl iodide,solvent is aprotic,polar and the nucleophile is a strong base.

Question 4

The step reaction polymerizations are fast polymerization reactions.

Question 5

Which of the following trends in nucleophilicity are correct?
I.Everything else being equal,a negatively charged nucleophile will react faster than a neutral one.
II.Generally,species containing elements of high electronegativity are good nucleophiles.
III.Anionic nucleophiles are more reactive in polar and aprotic solvents than in polar and protic solvents.
IV.Generally,nucleophilicity is increasing with the increase in size of an atom.
V.Bulky groups adjacent to the nucleophilic atom enhance the nucleophilicity and reactivity of the species.

A)I,II,III,and V
B)II,III,IV and V
C)I,II and IV
D)II,III and V
E)III,IV and V

Question 6

The alkanes are known for their reactivity.

Question 7

Which of the following steps can be found in E1 reaction mechanism?
I.formation of a carbocation
II.attack of the base and removal of a proton from carbocation
III.attack of a nucleophile
IV.formation of a carboanion

A)I and II
B)only II
C)I and III
D)III and IV
E)only III

Question 8

Nucleophiles are electron poor atoms,ions or groups.

Question 9

Which of the following statements correctly describe S_N2 and S_N1 reactions?
I.S_N2 reactions proceed with retention of configuration.
II.S_N1 reactions prefer polar protic solvents.
III.S_N1 reactions can produce racemic products.
IV.S_N2 reactions are promoted in the presence of a substrate that produces a very stable carbocation.
V.S_N1 reactions have a unimolecular rate-determining step.

A)I,IIand V.
B)II,III,and IV.
C)III,IV and V.
D)II,IIIand V.
E)I,III,and IV.

Question 10

S_N2 reactions are nucleophilic substitution reactions for which the rate determining step is bimolecular.

Question 11

The following can be said about the reaction profile of an S_N1 reaction:
I.The rate determining step is the formation of a carbocation.
II.The reaction profile has one transition state.
III.The slow step is the first transition state.
IV.The second step is attack of nuleophile on carbocation.
V.The reaction proceeds in a polar aprotic solvent.

A)I ,III ,and IV
B)I ,II and IV
C)II ,III and IV
D)I ,II and V
E)II,IV and V

Question 12

Organic reactions in which atoms or groups that are bonded to adjacent carbon atoms are eliminated are called elimination reactions.

Question 13

Molecules add across multiple bonds in another molecule in addition reactions.

Question 14

Arrange the following carbocations in order of decreasing stability:

A)A > B > C
B)C > B > A
C)B > C > A
D)C > A > B
E)B > A > C

Question 15

Arrange the following in the order of decreasing nucleophilicity:
H₂N^-,HO^-,HCOO^-,CH₃O^-

A)H₂N^- > HO^- > HCOO^- > CH₃O^-
B)H₂N^- > CH₃O^- > HO^- > HCOO^-
C)H₂N^- > HO^- > CH₃O^- > HCOO^-
D)HO^- > H₂N^- > CH₃O^- > HCOO^-
E)CH₃O^- > HO^- > H₂N^- > HCOO^-

Question 16

For which type of reaction is the following an example?

A)substitution
B)elimination
C)polymerization
D)rearrangement
E)addition

Question 17

Reactions between alkanes and HX compounds are typical examples of addition reactions.

Question 18

Finish the sentence:
"Elimination reactions...

A)...can follow two different mechanisms."
B)...do not compete with other reaction types."
C)...usually give a saturated product."
D)...always give only one product."
E)...have only one mechanistic path."

Question 19

We can promote S_N2 over S_N1 reactions if we:
I.use a substrate that gives a primary carbocation and not tertiary carbocation
II.use a sterically hindered substrate
III.use a polar protic solvent

A)I.
B)II.
C)III.
D)I and III.
E)II and III.

Question 20

In a substitution reaction an atom,an ion or a group in one molecule is replaced by another atom,ion or group.

Question 21

Which of the following compounds could be used as catalysts in halogenation of benzene?
I.AlCl₃
II.NaCl
III.FeBr₃
IV.MgCl₂
V.PbCl₂

A)I and V
B)II and III
C)II and IV
D)I and III
E)III and V

Question 22

During the nitration of a benzene ring in a mixture of HNO₃ and H₂SO₄ the following species reacts as an electrophile:

A)H₃O⁺
B)H₃SO₄⁺
C)H₂NO₃⁺
D)H⁺
E)NO₂⁺

Question 23

What product would you expect to obtain from a reaction between one isomer of 3-methyl-1-pentanol and HI?

A)a substitution product
B)only one elimination product
C)a substitution product with inversion of configuration
D)two elimination products
E)a racemic mixture of substitution products

Question 24

Which of the following could be added across carbon-carbon multiple bonds?
I.H₂SO₄
II.H₂
III.H₂O
IV.NO₂
V.HBr

A)II,III,and V
B)II,III,and IV
C)I,III,and V
D)I,III,and IV
E)I,II,and III

Question 25

Which of the following groups is a meta director during electrophilic aromatic substitution?

A)-NH₂
B)-OCH₃
C)-Br
D)-C≡N
E)-OCOC₂H₅

Question 26

A hydrocarbon has a molecular weight 56 g/mol and contains 85.7% carbon.It easily adds one mol of HBr to produce a chiral alkyl bromide.Which of the following structures could be the hydrocarbon?

A)
B)
C)
D)
E)

Question 27

What is the major product in the reaction between 2-bromo-3-methylbutane and KO^tBu in ethanol?

A)
B)
C)
D)
E)

Question 28

Which of the following roles can alcohols have in organic reactions?
I.electrophile
II.solvent
III.base
IV.substrate
V.acid

A)II,III and IV
B)I,II ,and III
C)I,III and V
D)II ,III and V
E)II ,IV and V

Question 29

Which of the following steps would you expect to occur in the addition reaction mechanism?
I.electrophilic attack on the unsaturated bond
II.formation of carboanion
III.formation of carbocation
IV.nucleophilic attack on the carbocation
V.elimination of a base

A)I ,III ,and IV
B)I ,II ,and V
C)II ,III and IV
D)III ,IV and V
E)II ,IV and V

Question 30

Find a group that is a ortho,para director in electrophilic aromatic substitution.

A)-NO₂
B)-SO₃H
C)-OH
D)-COOH
E)-COOCH₃

Question 31

The chlorination of benzaldehyde is producing:

A)m-chlorobenzaldehyde
B)a mixture of o and p- chlorobenzaldehyde
C)o -chlorobenzaldehyde
D)p-chlorobenzaldehyde
E)a mixture of m- and p-chlorobenzaldehyde

Question 32

Hyperconjugation is best described as:

A)an interaction between the orbitals on a substrate and orbitals on a nucleophile
B)an interaction between σ bonds and π network
C)a resonance structure with separated charges
D)an interaction between two π networks
E)an electrostatic interaction between an electrophile and a nucleophile

Question 33

Arrange the following alkenes according to their increasing stability:

A)A < B < C < D
B)B < C < A < D
C)B < A < C < D
D)C < B < A < D
E)C < A < B < D

Question 34

Which of the following is an unsymmetrical reagent?

A)Cl₂
B)H₂O
C)H₂O and HCl
D)HCl
E)I₂

Question 35

In which of the following reactions can alcohol participate?
I.oxidation reactions
II.elimination reactions
III.amide synthesis
IV.peptide synthesis
V.ester synthesis

A)I ,III and V
B)I ,II and V
C)II ,III and V
D)I ,II and IV
E)II ,III and IV

Question 36

Which of the following mechanistic steps do you expect in bromination of benzene with Br₂ and FeBr₃ as a catalyst?
I.formation of Br⁺[FeBr₄]^-
II.attack of [FeBr₄]^- on benzene ring
III.formation of arenium ion
IV.deprotonation of arenium ion
V.nucleophilic attack of Br⁺

A)I,III,and IV
B)I,II,and IV
C)II,III,and V
D)III,IV,and V
E)II,IV,and V

Question 37

What is a dehydration reaction?

A)Dehydration is the elimination of water molecule from an alcohol molecule to produce alkene.
B)A dehydration reaction is the removal of one equivalent of H₂ from an alkane to produce alkene.
C)A dehydration reaction is one of the steps in chain-reaction polymerization.
D)A dehydration reaction is the removal of crystalline water.
E)A dehydration reaction is the deprotonation of a substrate with a strong base in E2 mechanism.

Question 38

What is arenium ion?

A)a carbocation formed after the electrophilic attack on the benzene ring
B)a carbocation formed from a molecule containing an arene ring
C)a carbocation formed during the elimination reaction from an aromatic molecule
D)a carboanion formed from deprotonation of benzene ring
E)a carboanion formed after nucleophilic attack on the benzene ring

Question 39

Markovnikof's rule predicts that when HBr is added to an unsymmetrical alkene or alkyne,the H atom will add to which carbon atom?

A)the carbon with the fewest attached hydrogens
B)the carbon with the Br
C)the carbon with the most attached hydrogens
D)the carbon next to the double or triple bond
E)HBr does not react with unsymmetrical alkenes or alkynes

Question 40

The rate of E2 reaction between an alkyl halide RX and a base B is given by the following expression (k is a rate constant):

A)k[RX]
B)k[B]
C)k[RX][B]
D)k[RX]²
E)k[RX]²_[B]

Question 41

Identify the product(s)and mechanism for the following reaction:

A) S_N1 mechanism
B) S_N2 mechanism
C) S_N1 mechanism
D) S_N2 mechanism
E) S_N2 mechanism

Question 42

H₃C∙ + ∙Cl → H₃C-Cl is an example of:

A)polymerization
B)neutralization reaction
C)termination step in alkane chlorination
D)addition reaction
E)reforming reaction

Question 43

Predict the product and mechanism type for the following reaction:

A) S_N2 mechanism
B) S_N2 mechanism
C) S_N1 mechanism
D) S_N1 mechanism
E) S_N1 mechanism

Question 44

The formation of isopropanol (rubbing alcohol)through the following hydrolysis is known as what type of general reaction?

A)oxidation
B)aromatic substitution
C)addition reaction
D)elimination
E)substitution reaction

Question 45

Arrange the following radicals in the order of increasing stability:

A)B < A < C
B)C < A < B
C)A < B < C
D)C < B < A
E)B < C < A

Question 46

Which of the following statements correctly describe the step-reaction polymerization?
I.It is also called condensation polymerization.
II.It produces polymers of moderately high molecular masses.
III.It requires that monomers have functional groups that can join together.
IV.This type of polymerization is fast.
V.It is accompanied with the addition of a small molecule.

A)I ,II and III
B)I ,and II
C)II ,III and IV
D)III ,IV and V
E)II ,IV and V

Question 47

Which of the following are nucleophiles?
I.CH₃COCH₃
II.CH₃Br
III.CH₃CH₂C≡C^-

A)I
B)II
C)III
D)I + II
E)I + III

Question 48

The physical properties of polymers depend on:
I.the average molecular mass of a chain
II.the strength of intermolecular forces between the chains
III.the reaction temperature applied during synthesis
IV.the degree of crystallinity
V.the reaction pressure

A)I,II,and IV
B)II,III,and IV
C)I,II,and V
D)III,IV,and V
E)II,IV,and V

Question 49

Which of the following steps are a part of chain reaction during alkane substitution?
I.propagation
II.initiation
III.competition
IV.dehalogenation
V.termination

A)I,II and V
B)I,III and V
C)II,III and V
D)I,IIand IV
E)III,IV and V

Question 50

What is the rate law for the S_N1 reactions (S is substrate and N is nucleophile)?

A)rate = k[S][N]
B)rate = k[S]
C)rate = k[N]
D)rate = k[S]²
E)rate = k[S][N]²

Question 51

Chain reaction polymerization is typical for:

A)monomers with carbon-carbon double bonds
B)monomers with carbon oxygen double bonds
C)monomers containing aromatic rings
D)monomeric alkanes
E)monomeric alcohols

Question 52

What are the three characteristic steps in a chain-reaction polymerization?

A)initiation,elongation and termination
B)initiation,propagation and termination
C)racemization,propagation and quenching
D)propagation,formation and termination
E)breaking,elongation and quenching

Question 53

Suggest possible compounds for A,B and C in the following scheme:

A)A is Cl₂,B is AlCl₃ and C is meta chloronitrobenzene
B)A is Cl₂,B is FeCl₃ and C is ortho chloronitrobenzene
C)A is Cl₂,B is FeBr₃ and C is meta chloronitrobenzene
D)A is HCl,B is AlCl₃ and C is para chloronitrobenzene
E)A is Cl₂,B is AlBr₃ and C is meta chloronitrobenzene

Question 54

Which type of polymerization and which monomer(s)would you use to prepare poly(1,4-phenylenediformamide)with the following structure?

A) with chain reaction polymerization
B) with condensation polymerization
C) with chain reaction polymerization
D) with step-reaction polymerization
E) with chain reaction polymerization

Question 55

Suggest possible compounds for A and B in the following scheme:
CH₃CH₂I + A → CH₃CH₂SH + B

A)A is HS^- and B is I^-
B)A is H₂S and B is I₂
C)A is H₂S and B is HI
D)A is S^2- and B is I^-
E)A is H₂S and B is I^-

Question 56

Which of the following are electrophiles?
I.CH₃CH₂NH₂
II.Br⁺
III.CH₃OH

A)I
B)II
C)III
D)I + II
E)I + III

Question 57

Classify the following polymers as atactic,isotactic or syndiotactic:

A)Polymer A is isotactic,polymer B is atactic and polymer C is syndiotactic.
B)Polymer A is atactic,polymer B is isotactic and polymer C is syndiotactic.
C)Polymers A and B are isotactic and polymer C is syndiotactic.
D)Polymer A is isotactic and polymers B and C is syndiotactic.
E)Polymer A is syndiotactic,polymer B is isotactic and polymer C is atactic.

Question 58

What is "retrosynthesis"?

A)a chemical analysis followed by chemical synthesis
B)a chemical synthesis followed by chemical analysis
C)a synthetic procedure designed to check old synthetic procedure
D)a synthetic strategy that works from the desired compound towards starting materials
E)a synthetic strategy that works from the starting materials towards desired product

Question 59

The initiation step in chain reaction for alkene substitution produces:

A)free halogen radicals
B)free alkyl radicals
C)both free halogen and alkyl radicals
D)free halonium ions
E)free halide ions

Question 60

Complete the following reaction: NH₃ + CH₃Br →

A)CH₄ + NH₂Br
B)CH₂=NH + H₂ + HBr
C)CH₃NH₂ + NH₄⁺Br^-
D)CH₃NH₃⁺Br^-
E)There is no reaction.

Question 61

Give the product(s)of the reaction:
CH₂=CHCH₃ + HCl → product(s)

A)CH₃CH₂CH₃ + H₂
B)CH₂ClCHClCH₃ + H₂
C)CH₃CHClCH₃
D)CH₂ClCH₂CH₃
E)none of these

Question 62

Oxidation of the following alcohol via the conditions below yields spearmint oil.What new functional group is formed in the reaction to yield spearmint?

A)aldehyde
B)carboxylic acid
C)ketone
D)amine
E)ester

Question 63

Predict the major product for the reaction:
1-butene + HI →

A)CH₂ICH₂CH₂CH₃
B)CH₂ICH=CHCH₃
C)CH₂=CICH₂CH₃
D)CH₃CHICH₂CH₃
E)CH₃CI₂CH₂CH₃

Question 64

Suggest reagents for the synthesis of meta-chloronitrobenzene from nitrobenzene.

A)Cl₂ and AlCl₃
B)HCl and AlCl₃
C)Cl₂ and H₂SO₄
D)HCl and HNO₃
E)Cl₂ and FeBr₃

Question 65

Predict the major product for the reaction:
2-methyl-2-pentene + HCl →

A)(CH₃)₂CHCHClCH₂CH₃
B)CH₂=C(CH₃)CHClCH₂CH₃
C)(CH₃)₂CClCCl=CHCH₃
D)(CH₃)₂CClCH₂CH₂CH₃
E)no reaction

Question 66

What is the major product in the following transformation?

A)
B)
C)
D)
E)

Question 67

Lindlar's catalyst is used when ________.

A)we want to reduce alkynes to alkanes
B)we want to speed up HX addition reactions
C)we have to promote elimination reactions over substitution reactions
D)we need to activate Pd hydrogenation catalyst
E)we want to reduce alkynes to Z alkenes

Question 68

What alkene(s)would be produced in the following reaction?

A)3-methyl-2-pentene
B)2-methyl-2-butene
C)3-methylbutene
D)pentene and 1-methylpentene
E)2-methyl-2-butene and 3-methylbutene

Question 69

Predict the major product for the reaction:
2-methyl-2-butene + HBr →

A)(CH₃)₂CBrCH₂CH₃
B)(CH₃)₂CBrCH=CH₂
C)(CH₃)₂CHCHBrCH₃
D)CH₂=C(CH₃)CH₂CH₃
E)no reaction

Question 70

Identify the product for the following reaction:

A)3-methyl-1-pentene
B)3-methyl-2-pentene
C)3-methyl-1-pentane
D)3-methyl-1-tert-butylpentante
E)3-methylpentane

Question 71

The common general anesthetic neothyl can be produced by the following dehydration reaction.What is the systematic name of neothyl?
CH₃CH₂CH₂OH + CH₃OH ?

A)propanone
B)propanal
C)methyl propanoate
D)methyl propyl ether
E)ethyl methyl ether

Question 72

Predict the major product for the reaction:
CH₃C≡CH + 2 HBr →

A)CH₃CBr₂CH₃
B)CH₃CH₂CHBr₂
C)CH₃CHBrCH₂Br
D)CH₂=CBrCH₂Br
E)no reaction

Question 73

What is the main product of the following reaction?

A)1-bromopropane
B)2-bromopropane
C)propyl alcohol
D)2-bromopropene
E)1-bromo-2-methylethane

Question 74

Write down the rate law for E1 reactions (S is a substrate and B is a base).

A)rate = k[S]
B)rate = k[S][B]
C)rate = k[B]
D)rate = k[S]²
E)rate = k[S]^1/2

Question 75

Which are the most probable reactions and mechanisms in which tertiary haloalkanes participate?
I.Substitution,S_N1
II.Substitution S_N2
III.Elimination E1
IV.Elimination E2
V.Addition

A)II,III and IV
B)I,IV and V
C)II,III and V
D)I,III and IV
E)III,IV,V

Question 76

Order the following substrates according to the increase in S_N2 reaction rate:
(CH₃)₂CHBr, (CH₃)₃CBr,CH₃CH₂Br,CH₃Br

A)(CH₃)₂CHBr < (CH₃)₃CBr < CH₃CH₂Br < CH₃Br
B)(CH₃)₃CBr < (CH₃)₂CHBr < CH₃CH₂Br < CH₃Br
C)(CH₃)₃CBr < (CH₃)₂CHBr < CH₃Br < CH₃CH₂Br
D)(CH₃)₃CBr < CH₃CH₂Br < (CH₃)₂CHBr < CH₃Br
E)CH₃CH₂Br < (CH₃)₃CBr < (CH₃)₂CHBr < CH₃Br

Question 77

Give the correct mathematical expression for the rate law for E2 reactions (S is a substrate and B is a base).

A)rate = k[S]
B)rate = k[B]
C)rate = k[S][B]
D)rate = k[S]^1/2
E)rate = k[S]²

Question 78

When (CH₃)₃CBr reacts with CH₃ONa in methanol,two products are formed: a major one is an alkene and minor one is an ether.Identify the two products and by what mechanism(s)they are formed?

A)
B)
C)
D)
E)

Question 79

Which of the following alcohols can eliminate water to produce alkene?
I.phenol
II.HOC(CH₃)₃
III.HOCH(CH₃)₂

A)II and III
B)I ,II and III
C)III only
D)I and II
E)II only

Question 80

Give the product(s)of the reaction (in H₂SO₄):
CH₂=CHCH₃ + H₂O → product(s)

A)CH₂OHCH(OH)CH₃
B)CH₂OHCH₂CH₃
C)CH₂OHCHOHCH₃ + H₂
D)CH₃CH₂CH₃ + H₂O₂
E)CH₃CH(OH)CH₃