Question 1

Which of the following S_N2 reactions is the slowest?

Accepted Answer

Reaction B is the slowest because it involves a bimolecular nucleophilic substitution (SN2) reaction with water (a neutral nucleophile), which is generally slower than reactions involving charged nucleophiles like OH-.

Question 2

Which of the following is a secondary alkyl halide?

Accepted Answer

Option C represents a secondary alkyl halide because the carbon atom bonded to the bromine atom is also connected to two other carbon atoms, making it a secondary carbon.

Question 3

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

Accepted Answer

B

Question 4

Which of the following alkyl halides reacts the fastest in an S_N2 reaction?

Accepted Answer

In SN1 reactions, the rate of reaction is influenced by the stability of the carbocation intermediate and the bond strength between the carbon and the halogen. Iodine has the weakest C-I bond among the options, making 1-iodopropane the fastest to react due to easier formation of the carbocation intermediate.

Question 5

What is the nucleophile in the following reaction? 
I.

II. $\mathrm { H } _ { 2 } \mathrm { O }$

III. $\mathrm { H } _ { 3 } \mathrm { O } ^ { \oplus }$

IV. $\mathrm { I } ^ { \ominus }$

V. $\mathrm { HO } ^ { \ominus }$

Accepted Answer

The answer of What is the nucleophile in the following...

Question 6

$$\mathrm { CH } _ { 3 } \mathrm { Br } + \mathrm { HO }^ { \ominus } \longrightarrow \mathrm { CH } _ { 3 } \mathrm { OH } + \mathrm { Br }^ { \ominus }$$ -How does doubling the concentration of both the alkyl halide and the nucleophile in the above S_N2 reaction affect the rate of the reaction?

Accepted Answer

The reaction is second order overall (first order in each reactant), so doubling the concentration of both reactants quadruples the rate.

Question 7

Which of the following alkyl halides undergoes an S_N2 reaction most rapidly?

Accepted Answer

The SN2 reaction is favored by primary alkyl halides and better leaving groups. Iodine is a better leaving group than chlorine, and the primary iodide in option E is less hindered than the other options, making it the most reactive in an SN2 reaction.

Question 8

Which of the following S_N2 reactions is the slowest?

Accepted Answer

The answer of Which of the following S_N2 reactions is...

Question 9

Which of the following S_N2 reactions is the fastest?

Accepted Answer

The answer of Which of the following S_N2 reactions is...

Question 10

Which of the following is not a nucleophile?

Accepted Answer

Nucleophiles are species that donate a pair of electrons to form a chemical bond. Choice C, ${ } ^ { + } \mathrm { CH } _ { 3 }$, is a carbocation, which is an electron-deficient species and acts as an electrophile rather than a nucleophile.

Question 11

The specific rotation of $( R ) - \mathrm { C } _ { 6 } \mathrm { H } _ { 5 } \mathrm { CHOHCH } _ { 3 } \text { is } - 42.3 \text {. A pure sample of } ( R ) - \mathrm { C } _ { 6 } \mathrm { H } _ { 5 } \mathrm { CHClCH } _ { 3 }$ was converted into the corresponding alcohol via a S_N2 eaction. What is the specific rotation of the product?

Accepted Answer

In an SN2 reaction, inversion of configuration occurs. Since the starting material is (R)-C6H5CHClCH3, the product will be the (S)-alcohol, which has the opposite specific rotation of +42.3.

Question 12

Which of the following alkyl halides is the least reactive in an S_N2 reaction?

Accepted Answer

The answer of Which of the following alkyl halides is...

Question 13

The specific rotation of (R)-sec-butyl alcohol is -13.52. A pure sample of (R)-sec-butyl bromide was converted to sec-butyl alcohol via an S_N2 reaction. What is the specific rotation of The product, assuming 100% yield?

Accepted Answer

In an S_N2 reaction, inversion of configuration occurs. Thus, (R)-sec-butyl bromide will be converted to (S)-sec-butyl alcohol, which has a specific rotation of +13.52.

Question 14

Which of the following is not a nucleophile?

Accepted Answer

Nucleophiles are species that donate a pair of electrons to form a chemical bond. Options A, B, and C are all capable of donating electrons due to the presence of lone pairs or negative charges. Option D represents a positively charged species, which makes it an electrophile rather than a nucleophile, as it is more likely to accept electrons.

Question 15

What are the substitution products of the following reaction? 
$\mathrm { CH } _ { 3 } \mathrm { CH } _ { 2 } \mathrm { Br } + - \mathrm { OH } \rightarrow \text { ? }$

Accepted Answer

The reaction is a nucleophilic substitution where the hydroxide ion ($-\mathrm{OH}$) replaces the bromide ion ($\mathrm{Br}^-$) attached to the ethane molecule, resulting in ethanol ($\mathrm{CH}_3\mathrm{CH}_2\mathrm{OH}$) and a bromide ion as products.

Question 16

$$\mathrm { CH } _ { 3 } \mathrm { Br } + \mathrm { HO }^ { \ominus } \longrightarrow \mathrm { CH } _ { 3 } \mathrm { OH } + \mathrm { Br }^ { \ominus }$$ -How does doubling the concentration of the alkyl halide in the above S_N2 reaction affect the rate of the reaction?

Accepted Answer

The reaction is SN2, where the rate depends linearly on the concentration of both the alkyl halide and the nucleophile. Doubling the concentration of the alkyl halide ($\mathrm{CH}_3\mathrm{Br}$) therefore doubles the rate of the reaction.

Question 17

What product results from the S_N2 reaction between (R)-2-chloropentane and methoxide ion?

Accepted Answer

The reaction between (R)-2-chloropentane and methoxide ion involves an SN2 mechanism, which results in the inversion of configuration at the chiral center. Therefore, the product is (S)-2-methoxypentane.

Question 18

Which of the following alkyl halides reacts the fastest in an S_N2 reaction?

Accepted Answer

Chloromethane reacts the fastest in an S_N2 reaction because it is a primary alkyl halide with minimal steric hindrance, allowing the nucleophile to attack the carbon more easily.

Question 19

Which of the following S_N2 reactions is the fastest?

Accepted Answer

The answer of Which of the following S_N2 reactions is...

Question 20

Which of the following is the best nucleophile in an S_N2 reaction?

Accepted Answer

Ethoxide ion is the best nucleophile among the options because it is less hindered compared to tert-butoxide and tert-pentoxide ions, allowing it to attack the substrate more easily than the bulkier options. Isopropoxide ion is also less hindered but ethoxide ion is generally considered a stronger nucleophile due to its smaller size and ability to donate electrons more effectively.

Quiz 8: Substitution Reactions of Alkyl Halides

Which of the following S_N2 reactions is the slowest?

Which of the following is a secondary alkyl halide?

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

Which of the following alkyl halides reacts the fastest in an S_N2 reaction?

$\mathrm { CH } _ { 3 } \mathrm { Br } + \mathrm { HO }^ { \ominus } \longrightarrow \mathrm { CH } _ { 3 } \mathrm { OH } + \mathrm { Br }^ { \ominus }$ -How does doubling the concentration of both the alkyl halide and the nucleophile in the above S_N2 reaction affect the rate of the reaction?

Which of the following alkyl halides undergoes an S_N2 reaction most rapidly?

Which of the following S_N2 reactions is the slowest?

Which of the following S_N2 reactions is the fastest?

Which of the following is not a nucleophile?

Which of the following alkyl halides is the least reactive in an S_N2 reaction?

The specific rotation of (R) -sec-butyl alcohol is -13.52. A pure sample of (R) -sec-butyl bromide was converted to sec-butyl alcohol via an S_N2 reaction. What is the specific rotation of The product, assuming 100% yield?

Which of the following is not a nucleophile?

What are the substitution products of the following reaction? $\mathrm { CH } _ { 3 } \mathrm { CH } _ { 2 } \mathrm { Br } + - \mathrm { OH } \rightarrow \text { ? }$

$\mathrm { CH } _ { 3 } \mathrm { Br } + \mathrm { HO }^ { \ominus } \longrightarrow \mathrm { CH } _ { 3 } \mathrm { OH } + \mathrm { Br }^ { \ominus }$ -How does doubling the concentration of the alkyl halide in the above S_N2 reaction affect the rate of the reaction?

What product results from the S_N2 reaction between (R) -2-chloropentane and methoxide ion?

Which of the following alkyl halides reacts the fastest in an S_N2 reaction?

Which of the following S_N2 reactions is the fastest?

Which of the following is the best nucleophile in an S_N2 reaction?

Quiz 8: Substitution Reactions of Alkyl Halides

Which of the following SN2 reactions is the slowest?

Which of the following is a secondary alkyl halide?

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

Which of the following alkyl halides reacts the fastest in an SN2 reaction?

What is the nucleophile in the following reaction? I. II. H2O\mathrm { H } _ { 2 } \mathrm { O }H2​O III. H3O⊕\mathrm { H } _ { 3 } \mathrm { O } ^ { \oplus }H3​O⊕ IV. I⊖\mathrm { I } ^ { \ominus }I⊖ V. HO⊖\mathrm { HO } ^ { \ominus }HO⊖

Which of the following alkyl halides undergoes an SN2 reaction most rapidly?

Which of the following SN2 reactions is the slowest?

Which of the following SN2 reactions is the fastest?

Which of the following is not a nucleophile?

Which of the following alkyl halides is the least reactive in an SN2 reaction?

The specific rotation of (R) -sec-butyl alcohol is -13.52. A pure sample of (R) -sec-butyl bromide was converted to sec-butyl alcohol via an SN2 reaction. What is the specific rotation of The product, assuming 100% yield?

Which of the following is not a nucleophile?

What are the substitution products of the following reaction? CH3CH2Br+−OH→ ? \mathrm { CH } _ { 3 } \mathrm { CH } _ { 2 } \mathrm { Br } + - \mathrm { OH } \rightarrow \text { ? }CH3​CH2​Br+−OH→ ?

What product results from the SN2 reaction between (R) -2-chloropentane and methoxide ion?

Which of the following alkyl halides reacts the fastest in an SN2 reaction?

Which of the following SN2 reactions is the fastest?

Which of the following is the best nucleophile in an SN2 reaction?

Which of the following S_N2 reactions is the slowest?

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

Which of the following alkyl halides reacts the fastest in an S_N2 reaction?

Which of the following alkyl halides undergoes an S_N2 reaction most rapidly?

Which of the following S_N2 reactions is the slowest?

Which of the following S_N2 reactions is the fastest?

Which of the following alkyl halides is the least reactive in an S_N2 reaction?

The specific rotation of (R) -sec-butyl alcohol is -13.52. A pure sample of (R) -sec-butyl bromide was converted to sec-butyl alcohol via an S_N2 reaction. What is the specific rotation of The product, assuming 100% yield?

What are the substitution products of the following reaction? $\mathrm { CH } _ { 3 } \mathrm { CH } _ { 2 } \mathrm { Br } + - \mathrm { OH } \rightarrow \text { ? }$

What product results from the S_N2 reaction between (R) -2-chloropentane and methoxide ion?

Which of the following alkyl halides reacts the fastest in an S_N2 reaction?

Which of the following S_N2 reactions is the fastest?

Which of the following is the best nucleophile in an S_N2 reaction?