A substitution reaction is carried out on 2-iodobutane with sodium halide in alcohol solvent at 25°C, as follows: CH3CH2-CH(I)-CH3 + Nax Br or Cl) -(alcohol)-------> CH3CH2-CH(X)-CH3 + Nal (X = Based on the following observations, what is the most likely mechanism of this reaction? 1. The reaction rate is the same for NaCI and NaBr. 2. 2-methyl-2-iodobutane reacts faster with Nax under the same solvent/temperature conditions (mechanism is same as the 2-iodobutane reaction). Select one: A. A two-step substitution mechanism in which the 2nd step is slow and rate- determining. B. SN2 C. A two step mechanism in which X- bonds to C (bearing I) in step 1, followed by loss of I in step 2. D. SN1
A substitution reaction is carried out on 2-iodobutane with sodium halide in alcohol solvent at 25°C, as follows: CH3CH2-CH(I)-CH3 + Nax Br or Cl) -(alcohol)-------> CH3CH2-CH(X)-CH3 + Nal (X = Based on the following observations, what is the most likely mechanism of this reaction? 1. The reaction rate is the same for NaCI and NaBr. 2. 2-methyl-2-iodobutane reacts faster with Nax under the same solvent/temperature conditions (mechanism is same as the 2-iodobutane reaction). Select one: A. A two-step substitution mechanism in which the 2nd step is slow and rate- determining. B. SN2 C. A two step mechanism in which X- bonds to C (bearing I) in step 1, followed by loss of I in step 2. D. SN1
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![**Substitution Reaction Mechanism in Organic Chemistry**
When exploring substitution reactions, consider the example of a reaction carried out on 2-iodobutane with sodium halide in an alcoholic solvent at 25°C:
\[ \text{CH}_3\text{CH}_2\text{-CH(I)-CH}_3 + \text{NaX} \quad \xrightarrow{\text{(alcohol)}} \quad \text{CH}_3\text{CH}_2\text{-CH(X)-CH}_3 + \text{NaI} \]
(where \( \text{X} = \text{Br or Cl} \))
### Observations:
1. **Rate of Reaction**: The reaction rate remains unchanged for both NaCl and NaBr.
2. **Reactivity**: 2-methyl-2-iodobutane reacts more rapidly with NaX under identical solvent and temperature conditions, using a mechanism analogous to the 2-iodobutane reaction.
### Question:
What is the most likely mechanism for this reaction, based on the observed data?
**Options**:
- **A.** A two-step substitution mechanism where the second step is slow and rate-determining.
- **B.** \( S_N2 \) mechanism.
- **C.** A two-step mechanism in which \( \text{X}^- \) bonds to the carbon atom bearing iodine in the first step, succeeded by the loss of iodine in the second step.
- **D.** \( S_N1 \) mechanism.
Evaluate the options to determine the most plausible mechanism considering the effects of substrate structure, the leaving group, and the nature of the nucleophile involved.](/v2/_next/image?url=https%3A%2F%2Fcontent.bartleby.com%2Fqna-images%2Fquestion%2Fa7b7ae93-49f4-4302-b4e6-fcebec551689%2F4e546102-b121-445e-b349-26a157979f14%2F1n81t1zb_processed.png&w=3840&q=75)
Transcribed Image Text:**Substitution Reaction Mechanism in Organic Chemistry**
When exploring substitution reactions, consider the example of a reaction carried out on 2-iodobutane with sodium halide in an alcoholic solvent at 25°C:
\[ \text{CH}_3\text{CH}_2\text{-CH(I)-CH}_3 + \text{NaX} \quad \xrightarrow{\text{(alcohol)}} \quad \text{CH}_3\text{CH}_2\text{-CH(X)-CH}_3 + \text{NaI} \]
(where \( \text{X} = \text{Br or Cl} \))
### Observations:
1. **Rate of Reaction**: The reaction rate remains unchanged for both NaCl and NaBr.
2. **Reactivity**: 2-methyl-2-iodobutane reacts more rapidly with NaX under identical solvent and temperature conditions, using a mechanism analogous to the 2-iodobutane reaction.
### Question:
What is the most likely mechanism for this reaction, based on the observed data?
**Options**:
- **A.** A two-step substitution mechanism where the second step is slow and rate-determining.
- **B.** \( S_N2 \) mechanism.
- **C.** A two-step mechanism in which \( \text{X}^- \) bonds to the carbon atom bearing iodine in the first step, succeeded by the loss of iodine in the second step.
- **D.** \( S_N1 \) mechanism.
Evaluate the options to determine the most plausible mechanism considering the effects of substrate structure, the leaving group, and the nature of the nucleophile involved.
Transcribed Image Text:**Question:**
What is the organic product that forms in the following S<sub>N</sub>2 reaction?
**Reaction Diagram:**
- A linear molecule with a bromine (Br) and hydrogen (H) attached to a central carbon atom reacts with water (H<sub>2</sub>O) under S<sub>N</sub>2 conditions.
**Product Options:**
- Four structural isomers are provided as possible products:
**I.**
- A three-carbon chain with the hydroxyl (OH) group attached to the second carbon. Both hydrogens on that carbon are shown.
**II.**
- A three-carbon chain with the hydroxyl (OH) group attached to the first carbon (terminal carbon).
**III.**
- A similar structure to the reactant but with the hydroxyl (OH) group instead of the bromine (Br) on the second carbon.
**IV.**
- A three-carbon chain with the hydroxyl (OH) group also on a terminal carbon.
**Answer Options:**
- Select one:
- A. I
- B. II
- C. IV
- D. III
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