Question 1

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

Accepted Answer

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

Question 2

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

Question 3

What type of solvent is best for SN2 reactions which employ anionic nucleophiles: polar,protic solvents; polar,aprotic solvents; or nonpolar solvents? Explain.

Accepted Answer

Polar,aprotic solvents are bes

Question 4

Draw the alkene product which results when 1-bromopentane is heated in acetone containing NaOH.Give a detailed,step-by-step mechanism for the production of this compound.

Accepted Answer

The answer of Draw the alkene product which results when...

Question 5

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 6

Which of the following does not provide evidence that there are two different mechanisms for nucleophilic substitution?

Accepted Answer

A) reaction products when CH3I is used as the substrate 
B) reaction products when (CH3)3CCH2I is used as substrate 
C) the stereochemistry of nucleophilic substitutions 
D) the effect of nucleophile concentration on rate 
A) reaction products when CH3I is used as the substrate 
B) reaction products when (CH3)3CCH2I is used as substrate 
C) the stereochemistry of nucleophilic substitutions 
D) the effect of nucleophile concentration on rate

Question 7

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 8

Which of the following factors has no effect on the rate of SN1 reactions?

Accepted Answer

A) the nature of the alkyl halide 
B) the nature of the leaving group 
C) the concentration of the alkyl halide 
D) the concentration of the nucleophile 
E) the value of the rate constant 
A) the nature of the alkyl halide 
B) the nature of the leaving group 
C) the concentration of the alkyl halide 
D) the concentration of the nucleophile 
E) the value of the rate constant

Question 9

Give the major product for the following E2 reaction.

Accepted Answer

A)    
B)    
C)    
D)    
E) none of the above 
A)    
B)    
C)    
D)    
E) none of the above

Question 10

What is the major product of the following E2 reaction?

Accepted Answer

A)    
B) CH3CH2CH   CH2 
C)    
D)    
E)    
A)    
B) CH3CH2CH   CH2 
C)    
D)    
E)

Question 11

Assuming no other changes,what is the effect of doubling only the concentration of the nucleophile in the above 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 12

Provide the major organic product(s)of the reaction shown.

Accepted Answer

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

Question 13

Predict the two most likely mechanisms which occur when 2-iodohexane is heated in ethanol.

Accepted Answer

A) SN2 and SN1 
B) E1 and E2 
C) SN2 and E2 
D) E1 and SN1 
E) E2 and SN1 
A) SN2 and SN1 
B) E1 and E2 
C) SN2 and E2 
D) E1 and SN1 
E) E2 and SN1

Question 14

Assuming no other changes,what is the effect of doubling only the concentration of the alkyl halide in the above SN1 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 15

Provide the structure of the major elimination product which results when the alkyl bromide below is heated in ethanol.

Accepted Answer

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

Question 16

Give the name(s)of the product(s)of the SN2 reaction of 3-bromo-2,2-dimethylbutane with hydroxide.

Accepted Answer

A) 2,2-dimethyl-1-butanol 
B) 3,3-dimethyl-2-butanol 
C) 3,3-dimethyl-1-butanol 
D) 2,3-dimethyl-2-butanol 
E) 2,3-dimethyl-1-butanol 
A) 2,2-dimethyl-1-butanol 
B) 3,3-dimethyl-2-butanol 
C) 3,3-dimethyl-1-butanol 
D) 2,3-dimethyl-2-butanol 
E) 2,3-dimethyl-1-butanol

Question 17

Explain why SN2 reactions proceed faster in the solvent dimethylsulfoxide than in ethanol?
CH3SOCH3 CH3CH2OH
dimethlysolfoxide ethanol

Accepted Answer

Dimethlysulfoxide is an aproti

Question 18

Which of the following compounds will undergo an SN2 reaction most readily?

Accepted Answer

A) (CH3)3CCH2I 
B) (CH3)3CCl 
C) (CH3)2CHI 
D) (CH3)2CHCH2CH2CH2Cl 
E) (CH3)2CHCH2CH2CH2I 
A) (CH3)3CCH2I 
B) (CH3)3CCl 
C) (CH3)2CHI 
D) (CH3)2CHCH2CH2CH2Cl 
E) (CH3)2CHCH2CH2CH2I

Question 19

Provide a detailed,stepwise mechanism for the reaction below.
(CH3)2CHCH2CH2CH2I + CN- → (CH3)2CHCH2CH2CH2CN + I-

Accepted Answer

Question 20

Why,in a polar protic solvent,is iodide a better nucleophile than fluoride?

Accepted Answer

In addition to iodide being mo

Exam 9: Substitution and Elimination Reactions of Alkyl Halides

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

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

What type of solvent is best for SN2 reactions which employ anionic nucleophiles: polar,protic solvents; polar,aprotic solvents; or nonpolar solvents? Explain.

Draw the alkene product which results when 1-bromopentane is heated in acetone containing NaOH.Give a detailed,step-by-step mechanism for the production of this compound.

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

Which of the following does not provide evidence that there are two different mechanisms for nucleophilic substitution?

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

Which of the following factors has no effect on the rate of SN1 reactions?

Give the major product for the following E2 reaction.

What is the major product of the following E2 reaction?

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

Provide the major organic product(s)of the reaction shown.

Predict the two most likely mechanisms which occur when 2-iodohexane is heated in ethanol.

Assuming no other changes,what is the effect of doubling only the concentration of the alkyl halide in the above SN1 reaction?

Provide the structure of the major elimination product which results when the alkyl bromide below is heated in ethanol.

Give the name(s)of the product(s)of the SN2 reaction of 3-bromo-2,2-dimethylbutane with hydroxide.

Explain why SN2 reactions proceed faster in the solvent dimethylsulfoxide than in ethanol? CH3SOCH3 CH3CH2OH dimethlysolfoxide ethanol

Which of the following compounds will undergo an SN2 reaction most readily?

Provide a detailed,stepwise mechanism for the reaction below. (CH3)2CHCH2CH2CH2I + CN- → (CH3)2CHCH2CH2CH2CN + I-

Why,in a polar protic solvent,is iodide a better nucleophile than fluoride?

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

What type of solvent is best for S_N2 reactions which employ anionic nucleophiles: polar,protic solvents; polar,aprotic solvents; or nonpolar solvents? Explain.

Which of the following factors has no effect on the rate of S_N1 reactions?

Assuming no other changes,what is the effect of doubling only the concentration of the alkyl halide in the above S_N1 reaction?

Give the name(s)of the product(s)of the S_N2 reaction of 3-bromo-2,2-dimethylbutane with hydroxide.

Explain why S_N2 reactions proceed faster in the solvent dimethylsulfoxide than in ethanol? CH₃SOCH₃ CH₃CH₂OH dimethlysolfoxide ethanol

Which of the following compounds will undergo an S_N2 reaction most readily?

Provide a detailed,stepwise mechanism for the reaction below. (CH₃)₂CHCH₂CH₂CH₂I + CN^- → (CH₃)₂CHCH₂CH₂CH₂CN + I^-