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Chapter 9: Q74P (page 451)

Rank the following species in each set from best nucleophile to poorest nucleophile.

Short Answer

Expert verified

As the size of an atom is increased the more easily it can break the bond from its compound and behave as nucleophile.

Bigger size atom has more bond length so it can break easily the bond from its compound and attach with other compound.

Step by step solution

01

Reactivity depends upon size

As the size of an atom is increased the more easily it can break the bond from its compound and behave as nucleophile.

Bigger size atom has more bond length so it can break easily the bond from its compound and attach with other compound.

02

Final answer

As sulphur has bigger size than oxygen and in last nucleophile electrons will delocalize so it is not easy to break the bond.

In second nucleophile electrons will delocalize so it is not easy to break the bond.

Nitrogen is less electronegative than oxygen.

Bigger the size better is the nucleophile.

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Most popular questions from this chapter

Draw the substitution and elimination products for the following reactions, showing the configuration of each product:

a. trans-1-chloro-2-methylcyclohexane + CH3O-

b. cis-1-chloro-2-methylcyclohexane + CH3O鈭�

c. 1-chloro-1-methylcyclohexane + CH3O-

d. 1-chloro-1-methylcyclohexane + CH3OH

a. What is the major product obtained when each of the following compounds undergoes an E2 reaction with methoxide ion ? Show the configuration of the product.

b. Does the product obtained depend on whether you start with the R or S enantiomer of the reactant?

Which of the following reactions take place more rapidly when the concentration of the nucleophile is increased?

Draw the substitution products for each of the following reactions; if the products can exist as stereoisomers, show what stereoisomers are obtained:

a. ( R )-2-bromopentane + CH3O-

b. ( R )-3-bromo-3-methylheptane + CH3OH

c. benzyl chloride + CH3CH2OH

d. allyl chloride + CH3OH

e. 1-bromo-2-butene + CH3O-

f. 1-bromo-2-butene + CH3OH

How does the ratio of substitution product to elimination product formed from the reaction of propyl Bromide with CH3O- in methanol change if the nucleophile is changed to CH3S-?
See all solutions

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