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Chapter 12: 37E (page 385)

Assume that you are carrying out the base-induced dehydrobromination of 3-Bromo-3-methyl pentane (Section 11-7) to yield an alkene. How could you use IR spectroscopy to tell which of three possible elimination products is formed, if one includes E/Z isomers?

Short Answer

Expert verified

We can distinguish between monosubstituted alkene (3-methyl pentane), E, and Z-alkenes based on IR peaks.

Step by step solution

01

Base induced reaction

Base induced dehydrobromination of 3-Bromo-3-methyl pentane gives 3-methylpentane, (E)-3- methylpent-2-ene, and (z)-3-methylpent-2-ene which is represented as:

Base induced dehydrobromination

02

IR spectroscopy

This alkene show IR peaks between675鈭�1000鈥�cm鈭�1 due to bending of =C-H, but it depends on the substituents on the double bonds as follows:

  1. If the product is cis or Z isomer, it shows the IR peak 675鈭�750鈥�cm鈭�1.
  2. If the product is trans or E isomer, it shows the IR peak 920鈭�960鈥�cm鈭�1.
  3. If the product is disubstituted, it shows the IR peak860鈭�895鈥�cm鈭�1 .

Therefore, we can distinguish between monosubstituted alkene (3-methyl pentane), E, and Z-alkenes based on IR peaks.

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Most popular questions from this chapter

How would you prepare the following substances, starting from any

compounds having four carbons or fewer?

Name the following alkynes, and predict the products of their reaction

With:

(1) H2in the presence of a Lindlar鈥檚 catalyst

(2) H3O+in the presence of H2SO4

Where might the following compound have IR absorptions?

Question: Where might the following compound have IR absorptions?

Question: Two infrared spectra are shown. One is the spectrum of cyclohexane,

and the other is the spectrum of cyclohexene. Identify them, and

explain your answer.

(a)

(b)
See all solutions

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