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Chapter 11: Q.11-50e (page 350)


Question:What products would you expect from the reaction of 1-bromopropane with each of the following?

(e) Na+-C≡CH

Short Answer

Expert verified

Answer

CH3CH2CH2Br+Na+-C≡CH→CH3CH2CH2C≡CH+NaBrSubstitutionreaction

Step by step solution

01

SN2 reaction

It is a nucleophilic substitution reaction in which an old bond is broken and a new bond is formed. Both processes occur simultaneously. Hence, it is a single-step reaction.

Two reacting species are involved in the rate-determining steps

02

Reaction of CH3CH2CH2Br+Na+-C≡CH

It is a substitution reaction in which C-Br is broken and the C-C ≣H bond is formed in a single step process, which means the bromide ion is substituted by -C ≣H ion. Hence, it is a substitution reaction, and bromide and -C ≣H ion are nucleophiles’ so-called nucleophilic substitution reactions.

CH3CH2CH2Br+Na+-C≡CH→CH3CH2CH2C≡CH+NaBrSubstitutionreaction

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Most popular questions from this chapter

Tell whether each of the following reactions is likely to be SN1, SN2, E1, E1cB or E2:

a)

One step in the urea cycle for ridding the body of ammonia is the conversion of argininosuccinate to the amino acid arginine plus fumarate. Propose a mechanism for the reaction, and show the structure of arginine.

Methyl esters (RCO2CH3) undergo a cleavage reaction to yield carboxylate ions plus iodomethane on heating with LiI in dimethylformamide:

The following evidence has been obtained: (1) The reaction occurs much faster in DMF than in ethanol. (2) The corresponding ethyl ester (RCO2CH2CH3) cleaves approximately 10 times more slowly than the methyl ester. Propose a mechanism for the reaction. What other kinds of experimental evidence could you gather to support your hypothesis?

Write the product you would expect from reaction of each of the following alkyl halides with (1)Na+-SCH3and (2)Na+-OH (green = Cl):

b)

SN2 reactions take place with inversion of configuration, andSN1 reactions take place with racemization. The following substitution reaction, however, occurs with complete retention of configuration. Propose a mechanism.

.
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