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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

What is the major product formed when the following compounds undergo an E1 reaction?

a. Propose a mechanism for the following reaction.

b. Explain why two products are formed.

c. Explain why methanol substitutes for only one of the bromines.

Which alkyl halide in each pair is more reactive in an E2 reaction with hydroxide ion?

a. Draw the structures of the products obtained from the reaction of each enantiomer of cis-1-chloro-2-isopropylcyclopentane with sodium methoxide in methanol.

b. Are all the products optically active?

c. How would the products differ if the starting material were the trans isomer? Are these products optically active?

d. Will the cis enantiomers or the trans enantiomers form substitution products more rapidly?

e. Will the cis enantiomers or the trans enantiomers form elimination products more rapidly?

For each of the following reactions, draw the major elimination product; if the product can exist as stereoisomers, indicate which stereoisomer is obtained in greater yield.

a. (R)-2-bromohexane + high concentration of CH3O-

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

c. trans-1-chloro-2-methylcyclohexane + high concentration of CH3O-

d. trans-1-chloro-3-methylcyclohexane + high concentration of CH3O-

e. 3-bromo-3-methylpentane + high concentration of CH3CH2O-

f. 3-bromo-3-methylpentane + CH3CH2OH
See all solutions

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