Ch. 7 - Substitution ReactionsWorksheetSee all chapters
All Chapters
Ch. 1 - A Review of General Chemistry
Ch. 2 - Molecular Representations
Ch. 3 - Acids and Bases
Ch. 4 - Alkanes and Cycloalkanes
Ch. 5 - Chirality
Ch. 6 - Thermodynamics and Kinetics
Ch. 7 - Substitution Reactions
Ch. 8 - Elimination Reactions
Ch. 9 - Alkenes and Alkynes
Ch. 10 - Addition Reactions
Ch. 11 - Radical Reactions
Ch. 12 - Alcohols, Ethers, Epoxides and Thiols
Ch. 13 - Alcohols and Carbonyl Compounds
Ch. 14 - Synthetic Techniques
Ch. 15 - Analytical Techniques: IR, NMR, Mass Spect
Ch. 16 - Conjugated Systems
Ch. 17 - Aromaticity
Ch. 18 - Reactions of Aromatics: EAS and Beyond
Ch. 19 - Aldehydes and Ketones: Nucleophilic Addition
Ch. 20 - Carboxylic Acid Derivatives: NAS
Ch. 21 - Enolate Chemistry: Reactions at the Alpha-Carbon
Ch. 22 - Condensation Chemistry
Ch. 23 - Amines
Ch. 24 - Carbohydrates
Ch. 25 - Phenols
Ch. 26 - Amino Acids, Peptides, and Proteins

Solution: Rank the SN1 reaction rates for the following compounds:iodomethane, 2-iodo-2-methylhexane, 1-iodo-2-methylhexane, 3-iodo-2-methylhexane

Problem

Rank the SN1 reaction rates for the following compounds:

iodomethane, 2-iodo-2-methylhexane, 1-iodo-2-methylhexane, 3-iodo-2-methylhexane

Solution

We’re being asked to rank the reaction rates of each compound for an SN1 reaction.


Recall that the SN1 reaction occurs in two steps:

(1) carbocation formation – the carbon-leaving group bond is broken

(2) nucleophilic attack – the nucleophile donates its electron to the positively-charged carbon (electrophile)



Hyperconjugation from additional R-groups stabilizes the carbocation. This means a more substituted alkyl halide will have a faster reaction rate.


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