Question 1

Idenitfy the halide(s)that react in a SN1 reaction.
A)benzyl bromide
B)bromobenzene
C)1-bromo-1-butene
D)1-bromo-2-butene
E)2-bromo-2-phenylpropane

Accepted Answer

Question 2

Provide the structure of the major organic product of the following reaction.

Accepted Answer

The answer of Provide the structure of the major organic...

Question 3

Which of the following is a secondary alkyl halide?

Accepted Answer

A) CH3Br 
B) (CH3)3CBr 
C) (CH3)2CHBr 
D) (CH3)2CHCH2Br 
A) CH3Br 
B) (CH3)3CBr 
C) (CH3)2CHBr 
D) (CH3)2CHCH2Br

Question 4

Which of the following best explains why SN1 reactions involving a neutral reactant are faster in polar solvents?

Accepted Answer

A) The substrate is more soluble in polar solvents. 
B) The substrate is less soluble in polar solvents. 
C) The nucleophile is solvated by polar solvents. 
D) Solvation by polar solvents stabilizes the carbocation. 
E) Solvation by polar solvents stabilizes the transition state. 
A) The substrate is more soluble in polar solvents. 
B) The substrate is less soluble in polar solvents. 
C) The nucleophile is solvated by polar solvents. 
D) Solvation by polar solvents stabilizes the carbocation. 
E) Solvation by polar solvents stabilizes the transition state.

Question 5

Which of the following alkyl bromides undergoes solvolysis in methanol without rearrangement?

Accepted Answer

A) (R)-2-bromo-3-ethylpentane 
B) (S)-2-bromo-3-ethylpentane 
C) (R)-3-bromo-2-methylpentane 
D) (S)-3-bromo-2-methylpentane 
E) 3-bromo-3-ethylpentane 
A) (R)-2-bromo-3-ethylpentane 
B) (S)-2-bromo-3-ethylpentane 
C) (R)-3-bromo-2-methylpentane 
D) (S)-3-bromo-2-methylpentane 
E) 3-bromo-3-ethylpentane

Question 6

Assuming no other changes, what is the effect of doubling only the concentration of the alkyl halide in the above SN2 reaction?

Accepted Answer

A) no change 
B) doubles the rate 
C) triples the rate 
D) quadruples the rate 
E) rate is halved 
A) no change 
B) doubles the rate 
C) triples the rate 
D) quadruples the rate 
E) rate is halved

Question 7

The specific rotation of optically pure (R)-C6H5CHOHCH3 is -42.3°. An optically pure sample of (R)-C6H5CHClCH3 was converted into the corresponding alcohol via an SN2 reaction. What is the specific rotation of the product?

Accepted Answer

A) -42.3° 
B) between 0° and -42.3° 
C) between +42.3° and 0° 
D) +42.3° 
A) -42.3° 
B) between 0° and -42.3° 
C) between +42.3° and 0° 
D) +42.3°

Question 8

Which of the following correctly describes the relative nucleophilicities of methoxide and tert-butoxide?

Accepted Answer

A) These alkoxides have essentially the same nucleophilicities since the negative charge in both is localized on an oxygen atom. 
B) Methoxide is more nucleophilic because the nucleophilicity of tert-butoxide is diminished by steric effects. 
C) tert-Butoxide is more nucleophilic because it contains three methyl groups which increase the charge on its oxygen by donating electron density. 
D) tert-Butoxide is more nucleophilic because it is more basic. 
E) none of the above 
A) These alkoxides have essentially the same nucleophilicities since the negative charge in both is localized on an oxygen atom. 
B) Methoxide is more nucleophilic because the nucleophilicity of tert-butoxide is diminished by steric effects. 
C) tert-Butoxide is more nucleophilic because it contains three methyl groups which increase the charge on its oxygen by donating electron density. 
D) tert-Butoxide is more nucleophilic because it is more basic. 
E) none of the above

Question 9

Which of the following is not normally considered to be a nucleophile?

Accepted Answer

A) NH3 
B) NH2CH3 
C)    
D) CH3CH2+ 
A) NH3 
B) NH2CH3 
C)    
D) CH3CH2+

Question 10

Rank the species below in order of increasing nucleophilicity in protic solvents:
CH3CO2- , CH3S- , HO- , H2O.

Accepted Answer

H₂O < CH₃CO₂^-

Question 11

Which of the following best describes the carbon-chlorine bond of an alkyl chloride?

Accepted Answer

A) nonpolar; no dipole 
B) polar; δ+ at carbon and δ- at chlorine 
C) polar; δ- at carbon and δ+ at chlorine 
D) ionic 
E) none of the above 
A) nonpolar; no dipole 
B) polar; δ+ at carbon and δ- at chlorine 
C) polar; δ- at carbon and δ+ at chlorine 
D) ionic 
E) none of the above

Question 12

Why are vinylic halides unreactive in both SN2 and SN1 reactions?

Accepted Answer

Vinylic halides do not undergo S_N2 reacti

Question 13

Provide the structure of the major organic product of the following reaction.

Accepted Answer

The answer of Provide the structure of the major organic...

Question 14

Which of the following alkyl halides gives the slowest SN2 reaction?

Accepted Answer

A) CH3CH2Cl 
B)    
C)    
D)    
E)    
A) CH3CH2Cl 
B)    
C)    
D)    
E)

Question 15

Which of the following is not a nucleophile?

Accepted Answer

A) "CH3NH2" 
B) "PH3" 
C) "+CH3" 
D)    
E)    
A) "CH3NH2" 
B) "PH3" 
C) "+CH3" 
D)    
E)

Question 16

Which of the following is classified as a vinyl halide?

Accepted Answer

A) CH3CH   CHOH 
B) CH3CH   CHCl 
C) CH3CH   CHCH2Cl 
D) CH3CH2CH2CH2Br 
E) BrCH2CH   CH2 
A) CH3CH   CHOH 
B) CH3CH   CHCl 
C) CH3CH   CHCH2Cl 
D) CH3CH2CH2CH2Br 
E) BrCH2CH   CH2

Question 17

Provide the structure of the major organic product(s)of the following reaction.

Accepted Answer

The answer of Provide the structure of the major organic...

Question 18

Provide the major organic products(s)of the reaction shown:.

Accepted Answer

The answer of Provide the major organic products(s)of the reaction...

Question 19

A 1,2-methyl shift occurs when which of the following iodides is heated in ethanol?

Accepted Answer

A) C6H5CHICH(CH3)2 
B) (CH3)2CHCHICH3 
C) (CH3)3CCH2CH2I 
D) (CH3)2C=CHI 
E) (CH3)3CCHICH2CH3 
A) C6H5CHICH(CH3)2 
B) (CH3)2CHCHICH3 
C) (CH3)3CCH2CH2I 
D) (CH3)2C=CHI 
E) (CH3)3CCHICH2CH3

Question 20

When nucleophile and leaving group are contained in the same molecule, is intermolecular or intramolecular reaction favored? Explain.

Accepted Answer

The answer depends on the concentration

Exam 9: Substitution Reactions of Alkyl Halides

Idenitfy the halide(s)that react in a SN1 reaction. A)benzyl bromide B)bromobenzene C)1-bromo-1-butene D)1-bromo-2-butene E)2-bromo-2-phenylpropane

Provide the structure of the major organic product of the following reaction.

Which of the following is a secondary alkyl halide?

Which of the following best explains why SN1 reactions involving a neutral reactant are faster in polar solvents?

Which of the following alkyl bromides undergoes solvolysis in methanol without rearrangement?

Assuming no other changes, what is the effect of doubling only the concentration of the alkyl halide in the above SN2 reaction?

The specific rotation of optically pure (R)-C6H5CHOHCH3 is -42.3°. An optically pure sample of (R)-C6H5CHClCH3 was converted into the corresponding alcohol via an SN2 reaction. What is the specific rotation of the product?

Which of the following correctly describes the relative nucleophilicities of methoxide and tert-butoxide?

Which of the following is not normally considered to be a nucleophile?

Rank the species below in order of increasing nucleophilicity in protic solvents: CH3CO2- , CH3S- , HO- , H2O.

Which of the following best describes the carbon-chlorine bond of an alkyl chloride?

Why are vinylic halides unreactive in both SN2 and SN1 reactions?

Provide the structure of the major organic product of the following reaction.

Which of the following alkyl halides gives the slowest SN2 reaction?

Which of the following is not a nucleophile?

Which of the following is classified as a vinyl halide?

Provide the structure of the major organic product(s)of the following reaction.

Provide the major organic products(s)of the reaction shown:.

A 1,2-methyl shift occurs when which of the following iodides is heated in ethanol?

When nucleophile and leaving group are contained in the same molecule, is intermolecular or intramolecular reaction favored? Explain.

Remembering General Chemistry: Electronic Structure and Bonding

Acids and Bases: Central to Understanding Organic Chemistry

An Introduction to Organic Compounds

Isomers: the Arrangement of Atoms in Space

Alkenes Thermodynamics and Kinetics

Reactions of Alkenes

Reactions of Alkynes Introduction to Multistep Synthesis

Electron Delocalization, Resonance, and Aromaticity More About Molecular Orbital Theory

Elimination Reactions of Alkyl Halides Competition Between Substitution and Elimination

Reactions of Alcohols, Ethers, Epoxides, and Sulfur-Containing Compounds

Organometallic Compounds

Reactions of Alkanes, Radicals

Mass Spectrometry, Infrared Spectroscopy, and Uvvis Spectroscopy

Nmr Spectroscopy

Reactions of Carboxylic Acids and Carboxylic Acid Derivatives

Reactions of Aldehydes and Ketones

Reactions at the Alpha Carbon of Carbonyl Compounds

Reactions of Benzene and Substituted Benzenes

More About Amines Heterocylic Compounds

Carbohydrates

Amino Acids, Peptides, and Proteins

Catalysis

The Organic Mechanisms of the Coenzymes

The Chemistry of Metabolism

Nucleosides, Nucleotides, and Nucleic Acids

Synthetic Polymers

Pericyclic Reactions

Filters

Idenitfy the halide(s)that react in a S_N1 reaction. A)benzyl bromide B)bromobenzene C)1-bromo-1-butene D)1-bromo-2-butene E)2-bromo-2-phenylpropane

Which of the following best explains why S_N1 reactions involving a neutral reactant are faster in polar solvents?

Assuming no other changes, what is the effect of doubling only the concentration of the alkyl halide in the above S_N2 reaction?

The specific rotation of optically pure (R)-C₆H₅CHOHCH₃ is -42.3°. An optically pure sample of (R)-C₆H₅CHClCH₃ was converted into the corresponding alcohol via an S_N2 reaction. What is the specific rotation of the product?

Rank the species below in order of increasing nucleophilicity in protic solvents: CH₃CO₂^- , CH₃S^- , HO^- , H₂O.

Why are vinylic halides unreactive in both S_N2 and S_N1 reactions?

Which of the following alkyl halides gives the slowest S_N2 reaction?