1) Arrange the following halides reactivity toward an Sn2 reaction, and explain why each alkyl...


1) Arrange the following halides reactivity toward an Sn2 reaction, and explain why each alkyl halide has the fastest or slower or slowest reaction rate.

a) 1-Iodo-3-methyl butane

b) 2-Iodo-2-methyl butane

c) 2-Iodo-3-methyl butane

2) Draw the structures of the isomers produced by dehydration of 2-methylcycloheanol. Which one of these would be the most stable isomer according to Zaitsev's rule and GC analyses?

3) A student prepared 8.5ml of cyclohexene from 16.5ml of cyclohexanol by acid catalyzed dehydration. Write a balanced chemical equation for this reaction and calculate the percent yield of cyclohexene. Draw the structures and show all of the steps in the calculations.

  • Molar mass of cyclohexanol = 100.2g
  • Density = .962g/ml
  • Molar mass of cyclohexene = 82.14g
  • Density = .811g/ml

Substitution Reactions:

One of the easiest to imagine reactions is a substitution reaction, where one molecule approaches another, a bond begins to form, and a former substituent on one of the original molecules is ejected. These reactions can happen in two ways. The SN1 reaction type happens when the geometry of the reaction forbids a direct approach by the new substituent. Instead, the original one is dislodged, and the new one occupies its vacated spot shortly after. An SN2 reaction is a concerted mechanism; it's possible when the geometry is less obstructed: the new substituent approaches and the old one leaves simultaneously.

Answer and Explanation: 1

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1) The three options have the same substituents, but different arrangements.


  • 1-Iodo-3-methyl butane has a leaving group on the primary...

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Substitution Reaction Examples in Organic Chemistry


Chapter 10 / Lesson 23

Learn about substitution reactions in organic chemistry. Understand what a substitution reaction is, explore its two types, and see an example of both types.

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