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Chapter 9: Q24P (page 419)

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

Short Answer

Expert verified

1. It is a two step reaction.

2. In this carbocation is formed.

3. In this negative ion will attack from the side where there is less number of bulkier groups.

4. As the carbocation intermediate is formed so the stability order 3掳 carbocation>2掳 carbocation>1掳 carbocation

Step by step solution

01

How SN1 reaction proceed

1. It is a two step reaction.

2. In this carbocation is formed.

3. In this negative ion will attack from the side where there is less number of bulkier groups.

4. As the carbocation intermediate is formed so the stability order 3掳 carbocation>2掳 carbocation>1掳 carbocation

02

Final answer

a) In this secondary carbocation will form.

b) As bromine has greater size so it is better leaving group.

c) In this tertiary carbocation will form.

d) The other alkyl halide does not has B-hydrogens.

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Most popular questions from this chapter

Draw the configuration(s) of the substitution product(s) formed from the reaction of the following compounds with the indicated nucleophiles:

Indicate which species in each pair gives a higher substitution-product-to-elimination-product ratio when it reacts with isopropyl bromide:

a. ethoxide ion or tert-butoxide ion

b. -OCN or -SCN

c. Cl- or Br-

d. CH3S- or CH3O-

Amines are good nucleophiles, even though they are neutral. How would the rate of an SN2 reaction between an amine and an alkyl halide be affected if the polarity of the solvent is increased?

Draw the products of each of the following SN2/E2 reactions. If the products can exist as stereoisomers, show which stereoisomers are formed.

a.(3S,4S)-3-bromo-4-methylhexane + CH3O-

b.(3R,4R)-3-bromo-4-methylhexane + CH3O-

c.(3S,4R)-3-bromo-4-methylhexane + CH3O-

d.(3R,4S)-3-bromo-4-methylhexane + CH3O-

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
See all solutions

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