Question 1

Identify the strongest nucleophile in an SN2 reaction.

Accepted Answer

A) isopropoxide ion 
B) tert-butoxide ion 
C) ethoxide ion 
D) tert-pentoxide ion 
A) isopropoxide ion 
B) tert-butoxide ion 
C) ethoxide ion 
D) tert-pentoxide ion

Question 2

Which of the following statements correctly describe(s)E1 reactions of alkyl halides (RX)? 
I.Rate = k[base]
II.Rate = k[base][RX]
III.Rate = k[RX]
IV.The reactions occur in two distinct steps.
V.Rearrangements are sometimes seen.

Accepted Answer

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

Question 3

Provide the major organic product(s)in the reaction below.

Accepted Answer

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

Question 4

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 5

Which of the following compounds is/are the products of the following reaction?

Accepted Answer

A) I only 
B) II only 
C) I and II are of equal yield. 
D) I is major,II is minor. 
E) I is minor,II is major. 
A) I only 
B) II only 
C) I and II are of equal yield. 
D) I is major,II is minor. 
E) I is minor,II is major.

Question 6

How would you obtain the following two products from 1-bromo-1-methylcyclohexane?

Accepted Answer

The answer of How would you obtain the following two...

Question 7

In a SN1 reaction,carbocation is a(n)

Accepted Answer

A) transition state. 
B) catalyst. 
C) solvent. 
D) intermediate. 
E) side product. 
A) transition state. 
B) catalyst. 
C) solvent. 
D) intermediate. 
E) side product.

Question 8

Which of the alkyl chlorides listed below undergoes dehydrohalogenation in the presence of a strong base to give 2-pentene as the only alkene product?

Accepted Answer

A) 1-chloropentane 
B) 2-chloropentane 
C) 3-chloropentane 
D) 1-chloro-2-methylbutane 
E) 1-chloro-3-methylbutane 
A) 1-chloropentane 
B) 2-chloropentane 
C) 3-chloropentane 
D) 1-chloro-2-methylbutane 
E) 1-chloro-3-methylbutane

Question 9

Dehydrohalogenation of 2-bromobutane in the presence of a strong base proceeds via which of the following mechanistic pathways?

Accepted Answer

A) SN1 
B) SN2 
C) E1 
D) E2 
E) none of the above 
A) SN1 
B) SN2 
C) E1 
D) E2 
E) none of the above

Question 10

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 11

Consider the following experimental data for the rate of the reaction given below:     What is the mechanism for the reaction?

Accepted Answer

A) first order,SN1 
B) first order,SN2 
C) first order,E1 
D) first order,E2 
E) none of the above 
A) first order,SN1 
B) first order,SN2 
C) first order,E1 
D) first order,E2 
E) none of the above

Question 12

Starting with 2-butene,which of the following is the best method for preparing 2-butyne?

Accepted Answer

A) HBr; H2/Ni; Zn/H+ 
B) HBr; Zn/H+; H2/Ni 
C) Br2/CCl4; Zn/H+; H2/Ni 
D) Br2/CCl4; 2NaNH2 
E) HBr; NaNH2 
A) HBr; H2/Ni; Zn/H+ 
B) HBr; Zn/H+; H2/Ni 
C) Br2/CCl4; Zn/H+; H2/Ni 
D) Br2/CCl4; 2NaNH2 
E) HBr; NaNH2

Question 13

Draw product of the following intramolecular SN2 reaction.

Accepted Answer

Question 14

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

Accepted Answer

A) NH3 
B) NH2CH3 
C) HC   C:- 
D) CH3CH2+ 
A) NH3 
B) NH2CH3 
C) HC   C:- 
D) CH3CH2+

Question 15

A student attempted to prepare 1-chlorobutane by treating 1-butanol with NaCl in acetone.Was the student successful? Explain.

Accepted Answer

The student was unsuccessful.T

Question 16

Identify the major organic product for the reaction.

Accepted Answer

A)    
B) CH3CH2-C   CCH3 
C) CH3CH   C   CHCH3 
D) CH3CH2-CH2-CH   CH2 
E) CH3CH2-CH2-CH   CH 
A)    
B) CH3CH2-C   CCH3 
C) CH3CH   C   CHCH3 
D) CH3CH2-CH2-CH   CH2 
E) CH3CH2-CH2-CH   CH

Question 17

Which of the following are the elimination products of the reaction shown below? CH3CH2Br + -OH → ?

Accepted Answer

A) CH3CH2Br+H + O- 
B) HOCH2CH2Br 
C) CH3CH2OH + Br- 
D) CH2     CH2 + Br- + H2O 
E) CH2     CHBr + H2O 
A) CH3CH2Br+H + O- 
B) HOCH2CH2Br 
C) CH3CH2OH + Br- 
D) CH2     CH2 + Br- + H2O 
E) CH2     CHBr + H2O

Question 18

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 19

Identify the alkyl halide that reacts the fastest in an SN1 reaction.

Accepted Answer

A) 2-chloropropane 
B) 2-bromopropane 
C) 2-fluoropropane 
D) 2-iodopropane 
A) 2-chloropropane 
B) 2-bromopropane 
C) 2-fluoropropane 
D) 2-iodopropane

Question 20

Identify the mechanism.

Accepted Answer

A) SN1 
B) SN2 
C) E1 
D) E2 
E) none of the above 
A) SN1 
B) SN2 
C) E1 
D) E2 
E) none of the above

Exam 9: Substitution and Elimination Reactions of Alkyl Halides

Identify the strongest nucleophile in an SN2 reaction.

Which of the following statements correctly describe(s)E1 reactions of alkyl halides (RX)? I.Rate = k[base] II.Rate = k[base][RX] III.Rate = k[RX] IV.The reactions occur in two distinct steps. V.Rearrangements are sometimes seen.

Provide the major organic product(s)in the reaction below.

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

Which of the following compounds is/are the products of the following reaction?

How would you obtain the following two products from 1-bromo-1-methylcyclohexane?

In a SN1 reaction,carbocation is a(n)

Which of the alkyl chlorides listed below undergoes dehydrohalogenation in the presence of a strong base to give 2-pentene as the only alkene product?

Dehydrohalogenation of 2-bromobutane in the presence of a strong base proceeds via which of the following mechanistic pathways?

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

Consider the following experimental data for the rate of the reaction given below: What is the mechanism for the reaction?

Starting with 2-butene,which of the following is the best method for preparing 2-butyne?

Draw product of the following intramolecular SN2 reaction.

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

A student attempted to prepare 1-chlorobutane by treating 1-butanol with NaCl in acetone.Was the student successful? Explain.

Identify the major organic product for the reaction.

Which of the following are the elimination products of the reaction shown below? CH3CH2Br + -OH → ?

Which of the following is a secondary alkyl halide?

Identify the alkyl halide that reacts the fastest in an SN1 reaction.

Identify the mechanism.

Remembering General Chemistry: Electronic Structure and Bonding

Acids and Bases: Central to Understanding Organic Chemistry

An Introduction to Organic Compounds: Nomenclature, physical Properties, and Structure

Isomers: the Arrangement of Atoms in Space

Alkenes: Structure,nomenclature,and an Introduction to Reactivity - Thermodynamics and Kinetics

The Reactions of Alkenes - the Stereochemistry of Addition Reactions

The Reactions of Alkynes - Introduction to Multistep Synthesis

Delocalized Electrons: Their Effect on Stability, pka, and the Products of a Reaction - Aromaticity and Electronic Effects: an Introduction to the Reactions of Benzene

Reactions of Alcohols, ethers, epoxides, amines and Sulfur-Containing Compounds

Organometallic Compounds

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 Α-Carbon

Reactions of Benzene and Substituted Benzenes

More About Amines - Reactions of Heterocylic Compounds

The Organic Chemistry of Carbohydrates

Amino Acids,peptides,and Proteins

Catalysis in Organic Reactions and in Enzymatic Reactions

The Organic Chemistry of the Coenzymes, compounds Derived From Vitamins

The Organic Chemistry of the Metabolic Pathways

The Organic Chemistry of Lipids

The Chemistry of the Nucleic Acids

Synthetic Polymers

Pericyclic Reactions

Filters

Identify the strongest nucleophile in an S_N2 reaction.

In a S_N1 reaction,carbocation is a(n)

Draw product of the following intramolecular S_N2 reaction.

Which of the following are the elimination products of the reaction shown below? CH₃CH₂Br + ^-OH → ?

Identify the alkyl halide that reacts the fastest in an S_N1 reaction.