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Chapter 11: Q 11-11-41 E-b (page 350)

Which compound in each of the following pairs will react faster in an SN2reaction with OH-?

(b) CH3CH2Iin ethanol or dimethyl sulfoxide

Short Answer

Expert verified

CH3CH2I

Step by step solution

01

SN2 reaction

An old bond is broken and a new bond is formed in this nucleophilic substitution reaction. This occurs simultaneously. The reaction is therefore single-step.

The two reacting species are involved in the rate determining steps.

02

Nucleophile

Nucleophiles are the negatively charged ions or the neutral species having the lone pair of electrons ready for bonding.

03

Species react faster with OH-

If the species is a better leaving group, it reacts faster with the nucleophile.

I am a better leaving group than dimethyl sulfoxide (DMSO) in ethanol, aprotic solvent, and form hydrogen bonds with hydroxide. It decreases the reactivity of the reaction.

CH3CH2I shows fast reaction than DMSO

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Most popular questions from this chapter

Which reactant in each of the following pairs is more nucleophilic? Explain.

d) (CH3)3P or (CH3)3N

Among the many examples of reactions that occur with incomplete racemization, the optically pure tosylate of 2,2-dimethyl-1-phenyl-1-propan([ฮฑ]D= 230.3) gives the corresponding acetate ([ฮฑ]D= 15.3) when heated inacetic acid. If complete inversion had occurred, the optically pure acetatewould have had[ฮฑ]D= 153.6. What percentage racemization and what percentageinversion occurred in this reaction?

Which reactant in each of the following pairs is more nucleophilic? Explain.

(e) I- or Cl-

Question: Order each of the following sets of compounds with respect to reactivity:

b. (CH3)3 CCI (CH3)3 CBr (CH3)3 COH

Compound X is optically inactive and has the formulaC16H16Br2. On treatment with strong base, X gives hydrocarbon Y,C16H14. Compound Y absorbs 2 equivalents of hydrogen when reduced over a palladium catalyst and reacts with ozone to give two fragments. One fragment, Z, is an aldehyde with formulaC7H6O. The other fragment is glyoxal,(CHO)2. Write the reactions involved, and suggest structures for X, Y, and Z. What is the stereochemistry of X?
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