Organic Chemistry I

6.1
How many
1
H NMR signals would you predict for each of the following molecules?
6.2
Below are
13
C NMR spectra for methylbenzene (common name toluene) and methyl methacrylate. Refer to
Table
6.3
to match the spectra to the correct structure.
Answers to Practice Questions Chapter 6 | 237

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238 | Answers to Practice Questions Chapter 6

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CHAPTER 7 NUCLEOPHILIC SUBSTITUTION
REACTIONS
With the foundations have been built on the basic concepts in organic chemistry, we are now ready to learn about
organic reactions. Organic reaction is mainly about the transformation of one functional group to the other, that aims
to introduce new functional group into the product. As the reactivity center of a compound, a functional group has its
unique property and undergoes certain type of reaction. We will explore the certain rules that govern the reactivity of
each functional group, and understand why different functional groups show different reactivities. In this chapter, we
will start with substitution reaction of alkyl halide, and investigate further more from there.
Chapter 7 Nucleophilic Substitution Reactions | 239

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7.1 Nucleophilic Substitution Reaction Overview
Let’s start with a simple substitution reaction example:
Figure 7.1a Substitution reaction
In this reaction, the Br in the reactant methylbromide (CH
3
Br) is replaced by the OH group, and the methanol (CH
3
OH)
is produced as the major product, together with bromide Br-, the side product. It is easy to understand that this is a
substitution reaction, because Br is substituted by OH.
Further discussions on this simple reaction require the introduction of some key terms that are critical in
understanding why and how the reaction proceed in this way. These terms are electrophile, nucleophile and leaving
group.