7. Substitution Reactions

There were actually two possible products in the solvolysis reaction from Figure 21.10. Show both products. Which would you expect to be more stable? Why?

Two bromoethers are obtained from the reaction of the following alkyl dihalide with methanol. Draw the structures of the ethers.

Allylic halides have the structure

c. Show the products expected from S_N1 solvolysis of these halides in ethanol.

Propose a mechanism for each reaction, showing explicitly how the observed mixtures of products are formed.

(e) 3-chlorobut-1-ene + AgNO₃, H₂O → but-2-en-1-ol + but-3-en-2-ol

Which of the following alkyl halides would proceed with the fastest rate in an $S_{N1}$ reaction?

Predict the product of the following reaction:

Which of the following alkyl halides would be most reactive in an $S_{\mathrm{N1}}$ reaction?

Arrange the following compounds in order from fastest to slowest SN1 reaction rate: $t_1$-butyl chloride, isopropyl chloride, ethyl chloride.

Which of the following is a property of the $S{N}_1$ reaction mechanism?

Given two $S{N}_1$ reactions: (A) $R_1-\mathrm{Br}$ where $R_1$ is a tertiary alkyl group, and (B) $R_2-\mathrm{Br}$ where $R_2$ is a primary alkyl group. Both reactions occur in ethanol. Which reaction will proceed at a faster rate?

Which of the following is the major organic product formed when $t_1-\mathrm{butyl} \mathrm{bromide}$ reacts with water in an $S_1$ reaction?

Given the following compounds, order them from fastest to slowest in terms of $SN1$ reactivity (1 = fastest): (A) $C_6{H}_{5}CH2\mathrm{Br}$ (benzyl bromide), (B) $C_6{H}_5\mathrm{Br}$ (bromobenzene), (C) $t-\mathrm{BuBr}$ (tert-butyl bromide), (D) $\mathrm{CH}{3}_2\mathrm{CHBr}$ (isopropyl bromide). Which is the correct order?

Which of the following statements about an $S{N}_1$ reaction mechanism is true?

Which of the following alkyl halides is most likely to undergo rearrangement in an $S_{N1}$ reaction?

Propose an S_N1 mechanism for the solvolysis of 3-bromo-2,3-dimethylpentane in ethanol.