Question 1

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

Accepted Answer

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

Question 2

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

Accepted Answer

H₂O < CH₃CO₂^-

Question 3

Provide the major organic product of the following reaction.

Accepted Answer

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

Question 4

When (S)-2-bromobutane undergoes an SN2 reaction with CH3O-,the product is the compound shown below.What is/are the configuration(s)of the product(s)obtained from this reaction?

Accepted Answer

A) S only 
B) R only 
C) a mixture of enantiomers with more R than S 
D) a mixture of enantiomers with more S than R 
E) equal mixture of R and S 
A) S only 
B) R only 
C) a mixture of enantiomers with more R than S 
D) a mixture of enantiomers with more S than R 
E) equal mixture of R and S

Question 5

List the following compounds in order of increasing reactivity in an E1 elimination.
CH3CH2CHBrCH3,CH3CH2CH2CH2Br,(CH3)3CBr

Accepted Answer

CH₃(CH₂)₃Br <

Question 6

What is the nucleophile in the reaction shown below?

Accepted Answer

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

Question 7

When (S)-1-bromo-1 phenylethane undergoes an SN1 reaction with methanethiol (CH3SH),the product is the compound shown.What is/are the configuration(s)of the product obtained from this reaction?

Accepted Answer

A) S only 
B) R only 
C) a mixture of the enantiomers,with slightly more S than R 
D) a mixture of the enantiomers,with slightly more R than S 
A) S only 
B) R only 
C) a mixture of the enantiomers,with slightly more S than R 
D) a mixture of the enantiomers,with slightly more R than S

Question 8

Which of the compounds below undergoes solvolysis in aqueous ethanol most rapidly?

Accepted Answer

A) cyclohexyl bromide 
B) methyl iodide 
C) isopropyl chloride 
D) 3-chloropentane 
E) 3-iodo-3-methylpentane 
A) cyclohexyl bromide 
B) methyl iodide 
C) isopropyl chloride 
D) 3-chloropentane 
E) 3-iodo-3-methylpentane

Question 9

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 10

Which of the following is the strongest nucleophile in an aqueous solution?

Accepted Answer

A) HO- 
B) F- 
C) Cl- 
D) Br- 
E) I- 
A) HO- 
B) F- 
C) Cl- 
D) Br- 
E) I-

Question 11

How many distinct alkene products are formed in this reaction?

Accepted Answer

A) 0 
B) 1 
C) 2 
D) 3 
E) 4 
A) 0 
B) 1 
C) 2 
D) 3 
E) 4

Question 12

Give the mechanism of the reaction shown below.

Accepted Answer

The answer of Give the mechanism of the reaction shown...

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

What is the major product of the following reaction?

Accepted Answer

A) CH2     CHCH2CH3 
B) CH3CH   CHCH3 
C)    
D) CH3CH2CH2CH2OCH2CH3 
E)    
A) CH2     CHCH2CH3 
B) CH3CH   CHCH3 
C)    
D) CH3CH2CH2CH2OCH2CH3 
E)

Question 15

Identify the alkyl halide that reacts the fastest in a SN2 reaction.

Accepted Answer

A) 2-chloro-2-methylpropane 
B) 2-chlorobutane 
C) 1-chlorobutane 
D) chloromethane 
A) 2-chloro-2-methylpropane 
B) 2-chlorobutane 
C) 1-chlorobutane 
D) chloromethane

Question 16

Which of the following halides is least reactive in an E2 reaction with sodium methoxide?

Accepted Answer

A) (CH3)3CCH2I 
B) (CH3)2CHCHICH3 
C) (CH3)2CHCH2Br 
D) (CH3)2CHCH2Cl 
E) (CH3)2CHCH2CH2Cl 
A) (CH3)3CCH2I 
B) (CH3)2CHCHICH3 
C) (CH3)2CHCH2Br 
D) (CH3)2CHCH2Cl 
E) (CH3)2CHCH2CH2Cl

Question 17

Provide the structure of the major organic products which result in the reaction below.

Accepted Answer

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

Question 18

Give the name(s)of the product(s)for the following SN1 reactions.You may choose more than one answer.

Accepted Answer

A) (S)-2-hexanol 
B) (R)-2-hexanol 
C) (S)-3-hexanol 
D) (R)-3-hexanol 
A) (S)-2-hexanol 
B) (R)-2-hexanol 
C) (S)-3-hexanol 
D) (R)-3-hexanol

Question 19

Give the product from the reaction of 1-pentene with the following reagents.
1.Cl2
2.-OH
3.NaNH2
4.CH3CH2Br

Accepted Answer

Question 20

Which of the following species is most reactive in an SN2 reaction?

Accepted Answer

A) CH3CH2-Cl 
B) CH3CH2-Br 
C) CH3CH2-I 
D) CH3CH2-F 
E) CH3CH2-OH 
A) CH3CH2-Cl 
B) CH3CH2-Br 
C) CH3CH2-I 
D) CH3CH2-F 
E) CH3CH2-OH

Exam 9: Substitution and Elimination Reactions of Alkyl Halides

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

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

Provide the major organic product of the following reaction.

When (S)-2-bromobutane undergoes an SN2 reaction with CH3O-,the product is the compound shown below.What is/are the configuration(s)of the product(s)obtained from this reaction?

List the following compounds in order of increasing reactivity in an E1 elimination. CH3CH2CHBrCH3,CH3CH2CH2CH2Br,(CH3)3CBr

What is the nucleophile in the reaction shown below?

When (S)-1-bromo-1 phenylethane undergoes an SN1 reaction with methanethiol (CH3SH),the product is the compound shown.What is/are the configuration(s)of the product obtained from this reaction?

Which of the compounds below undergoes solvolysis in aqueous ethanol most rapidly?

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 is the strongest nucleophile in an aqueous solution?

How many distinct alkene products are formed in this reaction?

Give the mechanism of the reaction shown below.

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

What is the major product of the following reaction?

Identify the alkyl halide that reacts the fastest in a SN2 reaction.

Which of the following halides is least reactive in an E2 reaction with sodium methoxide?

Provide the structure of the major organic products which result in the reaction below.

Give the name(s)of the product(s)for the following SN1 reactions.You may choose more than one answer.

Give the product from the reaction of 1-pentene with the following reagents. 1.Cl2 2.-OH 3.NaNH2 4.CH3CH2Br

Which of the following species is most reactive in an SN2 reaction?

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

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

When (S)-2-bromobutane undergoes an S_N2 reaction with CH₃O^-,the product is the compound shown below.What is/are the configuration(s)of the product(s)obtained from this reaction?

List the following compounds in order of increasing reactivity in an E1 elimination. CH₃CH₂CHBrCH₃,CH₃CH₂CH₂CH₂Br,(CH₃)₃CBr

When (S)-1-bromo-1 phenylethane undergoes an S_N1 reaction with methanethiol (CH₃SH),the product is the compound shown.What is/are the configuration(s)of the product obtained from this 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?

Identify the alkyl halide that reacts the fastest in a S_N2 reaction.

Give the name(s)of the product(s)for the following S_N1 reactions.You may choose more than one answer.

Give the product from the reaction of 1-pentene with the following reagents. 1.Cl₂ 2.^-OH 3.NaNH₂ 4.CH₃CH₂Br

Which of the following species is most reactive in an S_N2 reaction?