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4. Provide the product/s for the following reactions. Indicate if the reactions proceed via an SNI, or SN2 mechanism. Indicate proper stereochemistry if it is applicable. Show the mechanisms. NaCN DMF b) NASH DMSO ČI „Br NaOH c) DMSO

4. Provide the product/s for the following reactions. Indicate if the reactions proceed via an SNI, or SN2 mechanism. Indicate proper stereochemistry if it is applicable. Show the mechanisms. NaCN DMF b) NASH DMSO ČI „Br NaOH c) DMSO

Chemistry
Chemistry
10th Edition
ISBN:9781305957404
Author:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Publisher:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Chapter1: Chemical Foundations
Section: Chapter Questions
Problem 1RQ: Define and explain the differences between the following terms. a. law and theory b. theory and...
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parts a, b, and c

**Question 4:** Provide the product(s) for the following reactions. Indicate if the reactions proceed via an SN1 or SN2 mechanism. Indicate proper stereochemistry if it is applicable. Show the mechanisms. **a)** The compound is 2-chloroheptane, which reacts with sodium cyanide (NaCN) in dimethylformamide (DMF). **b)** The compound is cyclohexyl chloride, which reacts with sodium hydrogen sulfide (NaSH) in dimethyl sulfoxide (DMSO). **c)** The compound is 1-bromobutane, which reacts with sodium hydroxide (NaOH) in DMSO. **Explanations/Diagrams:** - For **a), b),** and **c)**, explain the mechanism (SN1 or SN2) based on the presence of substrate type (primary, secondary, or tertiary carbon centers), leaving groups, and nucleophiles. - **SN2 Mechanism Details:** Involves a one-step bimolecular nucleophilic substitution, leading to inversion of configuration if applicable. - **SN1 Mechanism Details:** Involves a two-step process with carbocation intermediate formation, leading to racemization if a chiral center is involved. Graphs or diagrams are not provided, but drawings of the mechanisms can illustrate the substitution process with electron movement (arrows) and any intermediate steps. Consider the attack of the nucleophile, departure of the leaving group, and any stereochemical outcomes such as inversion of configuration.
Transcribed Image Text:**Question 4:** Provide the product(s) for the following reactions. Indicate if the reactions proceed via an SN1 or SN2 mechanism. Indicate proper stereochemistry if it is applicable. Show the mechanisms. **a)** The compound is 2-chloroheptane, which reacts with sodium cyanide (NaCN) in dimethylformamide (DMF). **b)** The compound is cyclohexyl chloride, which reacts with sodium hydrogen sulfide (NaSH) in dimethyl sulfoxide (DMSO). **c)** The compound is 1-bromobutane, which reacts with sodium hydroxide (NaOH) in DMSO. **Explanations/Diagrams:** - For **a), b),** and **c)**, explain the mechanism (SN1 or SN2) based on the presence of substrate type (primary, secondary, or tertiary carbon centers), leaving groups, and nucleophiles. - **SN2 Mechanism Details:** Involves a one-step bimolecular nucleophilic substitution, leading to inversion of configuration if applicable. - **SN1 Mechanism Details:** Involves a two-step process with carbocation intermediate formation, leading to racemization if a chiral center is involved. Graphs or diagrams are not provided, but drawings of the mechanisms can illustrate the substitution process with electron movement (arrows) and any intermediate steps. Consider the attack of the nucleophile, departure of the leaving group, and any stereochemical outcomes such as inversion of configuration.
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