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Chapter 7: Q 20P (page 360)

Give the substitution and elimination products you would expect from the following reactions.

  1. 3-bromo-3-ethylpentane heated in methanol
  2. 1-iodo-1-phenylcyclopentane heated in ethanol
  3. 1-bromo-2-methylcyclohexane + silver nitrate in water (forces ionization)

Short Answer

Expert verified

a.

Substitution Elimination

Product Product

b.

Substitution Elimination

Product Product

c.

Elimination Minor

Product product product

With rearrangement

Step by step solution

01

Step by step solution:  Step 1: Explanation of part (a)

When 3-bromo-3-ethylpentane is heated with methanol, substitution as well as elimination reaction can take place. reaction occurs as tertiary carbocation is formed when leaving group bromine leaves. Then, methanol acts as nucleophile and attacks carbocation which leads to formation of substitution product. Elimination product is also possible, because after carbocation formation, the adjacent carbon鈥檚 hydrogen can stabilize positive charge on carbocation by forming double bond. E1 product will be obtained.

Substitution product Elimination Product

02

Step-2. Explanation of part (b)

When 1-iodo-1-phenylcyclopentane is heated in ethanol, substitution as well as elimination reaction can occur. reaction occurs as tertiary carbocation is formed when leaving group iodine leaves. Then, ethanol acts as nucleophile and attacks carbocation and this leads to formation of substitution product. Elimination product is also possible, because after carbocation formation, the adjacent carbon鈥檚 hydrogen can stabilize positive charge; and ethanol abstracts this proton and forms a double bond. E1 product will be obtained.

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Most popular questions from this chapter

Predict the elimination products of the following reactions and label the major products.

  1. Cis-1-bromo-2-methylcyclohexane +in
  2. Trans-1-bromo-2-methylcyclohexane +in

Show that the (S,S) enantiomer of this (R,R) diastereomer of 1-bromo-1,2-diphenylpropane also undergoes E2 elimination to give the cis diastereomer of the product. (We do not expect these achiral reagents to distinguish between enantiomers.)

When 2-bromo-3-phenylbutane is treated with sodium methoxide, two alkenes result (by E2 elimination). The Zaitsev product predominates.

  1. Draw the reaction, showing the major and minor products.
  2. When one pure stereoisomer of 2-bromo-3-phenylbutane reacts, one pure stereoisomer of the major product results. For example, when (2R,3R)-2-bromo-3-phenylbutane reacts, the product is the stereoisomer with the methyl group cis. Use your models to draw a Newmanprojection of the transition state to show why this stereospecificity is observed.
  3. Use a Newman projection of the transition state to predict the major product of elimination of (2S,3R)-2-bromo-3-phenylbutane.
  4. Predict the major product from elimination of (2S,3S)-2-bromo-3-phenylbutane. This prediction can be made without drawing any structures, by considering the results in part (b).

Propose mechanisms and draw reaction-energy diagrams for the following reactions. Pay particular attention to the structures of any transition states and intermediates. Compare the reaction-energy diagrams for the two reactions and explain the differences.

  1. 2-Bromo-2-methylbutane reacts with sodium methoxide in methanol to give 2-methylbut-2-ene (among other products).
  2. 2-Bromo-2-methylbutane reacts in boiling methanol to give 2-methylbut-2-ene (among other products).

Show how you would convert (in one or two steps) 1-phenylpropane to the three products shown below. In each case, explain what unwanted reactions might produce undesirable impurities in the product.
See all solutions

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