How to Choose Molecules for Doing SN2 and SN1 Synthesis-Practice Problems
Practice
Identify the reagents that would allow accomplishing each of the following transformations. More than one reagent and one step may be required. Pay close attention to the stereochemistry. As a good practice, determine if the reaction goes through SN1 or SN2 mechanism and draw the curved arrow mechanisms.

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Each of the following compounds can be prepared with an alkyl halide and a suitable nucleophile by SN2 substitution. Identify the alkyl halide and the nucleophile that would lead to each product. When more than one set of reactants can be used, determine which one is a better choice.

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Check Also
- Introduction to Alkyl Halides
- Nomenclature of Alkyl Halides
- Substitution and Elimination Reactions
- Nucleophilic Substitution Reactions – An Introduction
- The SN2 Mechanism: Kinetics, Thermodynamics, Curved Arrows, and Stereochemistry with Practice Problems
- The Stereochemistry of SN2 Reactions
- Stability of Carbocations
- The SN1 Nucleophilic Substitution Reaction
- Reactions of Alkyl Halides with Water
- The Stereochemistry of the SN1 Reaction Mechanism
- The SN1 Mechanism: Kinetics, Thermodynamics, Curved Arrows, and Stereochemistry with Practice Problems
- Steric Hindrance in SN2 and SN1 Reactions
- Carbocation Rearrangements in SN1 Reactions with Practice Problems
- Ring Expansion Rearrangements
- Ring Contraction Rearrangements
- When Is the Mechanism SN1 or SN2?
- Reactions of Alcohols with HCl, HBr, and HI Acids
- SOCl2 and PBr3 for Conversion of Alcohols to Alkyl Halides
- Alcohols in SN1 and SN2 Reactions
- How to Choose Molecules for Doing SN2 and SN1 Synthesis-Practice Problems
- Exceptions in SN2 and SN1 Reactions
- SN1 vs E1 Reactions
- SN2 vs E2 Reactions
- Dehydration of Alcohols by E1 and E2 Elimination
- Mesylates and Tosylates as Good Leaving Groups
- Mitsunobu Reaction
- SN1 SN2 E1 E2 – How to Choose the Mechanism
- Polar Protic and Polar Aprotic Solvents
- SN1 SN2 E1 or E2 – the Largest Collection of Practice Problems
- Nucleophilic Substitution and Elimination Practice Quiz
- Reactions Map of Alkyl Halides
Hello Professor: If I react 5-bromo-2-methyl-2-hexene with water in an SN1, would the rearrangement of a carbocation to an allylic cation lead me to (E)-2-methyl-3-ene-2-ol?
Hello Frank,
Yes, I have replied to this question here.