a. 2-chlorobutane b. 2-methyl-2-chlorobutane c. 1-chlorobutane you expect to be

Question

a. 2-chlorobutane b. 2-methyl-2-chlorobutane c. 1-chlorobutane you expect to be most reactive in an SN2 reaction? chloromethane 2. Which of the following statements is most TRUE regarding the reaction shown below? b. Thi c. Thi d. This is reaction likely proceeds using and SN1-based mechanism s reaction likely proceeds using an E1-based mechanism s reaction likely proceeds using-OH as a leaving group s reaction would proceed using an anti-periplanar transition state 3. Which of the following statements regarding substitution/elimination mechanisms is most TRUE? a. The first step of an E2 and SN2 reaction is the same b. The rate limiting step of an E1 reaction is the removal of a proton from the substrate by c. Primary substrates are appropriate for SN2 and E1 reactions due to the low steric d. Performing a substitution reaction on a secondary substrate with a strong nucleophile a base hindrance around the alpha-carbon. would promote an SN2 reaction over an Sw1 reaction. 4. Which of the following statements regarding substitution/elimination mechanisms is most TRUE? a. The product of an SN2 reaction often possesses the opposite stereochemistry of the original substrate. b. The use of a polar protic solvent would be an appropriate choice for an SN2 reaction due to increased solvation and stabilization of the nucleophile which is an important component of the SN2 mechanism c. A racemic mixture is often the result of SN2 and SN1-based substitutions d. The oTos substituent is an excellent nucleophile 5. Which of the following molecules is a good example of an allylic/benzylic alcohol a. 1-butanol b. benzoic acid c. ethylene glycol d. phenol

Explanation / Answer

1) chloromethane is most reactive in SN2 reaction.

Explanation: SN2 reaction is best given by simple and sterically less hindered alkyl halides. 2-chlorobutane is secondary alkyl halides, 2-methyl-2-chlorobutane is a tertiary alkyl halide, 1-chlorobutane is primary alkyl halide and chloromethane is a primary and simple alkyl halide. so chloromethane is most reactive in SN2 reaction.

2) option A is correct

3) option D is true.

Explanation: reaction os secondary alkyl halide with a strong nucleophile gives SN2 mechanism. so option D is correct.

SN2 and E2 reactions are concerted mechanisms so the first step is not same for these two recations so option A is not true.

The rat elimiting step of E1 reaction is elimination of leaving group to form carbocation as an intermediate. so option B is not true.

E1 reactions invovle tertiary substrates so option C is not true.

4) optioon A is correct.

Explanation: SN2 reactions invovles inversion of configuration and produces product with opposite configuration to substrate.

5) option B is correct.

benzoic acid on reduction produces benzylic alcohol.

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