Exam 9: The Chemistry of Alkyl Halides

Consider the reaction: a. On the left side of the equation, draw the curved-arrow notation for the reaction in the left-to-right direction. b. On the left side of the equation, circle the nucleophile and label it "N." c. On the left side of the equation, circle the electrophilic atom and label it "E." d. On the left side of the equation, circle the leaving group and label it "LG."

Which compound will undergo the fastest S_N1/E1 reaction in methanol, a protic solvent?

Write the mechanism of the reaction (that is, S_N2, S_N1, E2, E1) that is required to form each product in the reaction:

Predict the organic product(s) of the reaction and give the shorthand for mechanism (that is, E1, E2, S_N1, S_N2) by which each is formed.

Write the two possible -elimination products formed in the reaction:

Which compound undergoes the fastest S_N1 solvolysis reaction with water in acetone?

Which compound undergoes the fastest S_N2 reaction with Na⁺ CH₃O⁻?

Which compound will be most reactive in the S_N2 reaction with EtO⁻ Na⁺ in EtOH?

Give the structure of the nucleophile that would give the product shown in the S_N2 reaction. Show any charges or unshared valence electrons. Then give the curved-arrow notation for the reaction. (Show it on the diagram.)

Which species would act as the best (most reactive) nucleophile toward methyl iodide in a polar aprotic solvent?

Which of these compounds will undergo the most rapid solvolysis reaction in methanol? (No base is added.)

When we say, "sodium ethoxide (Na⁺ EtO⁻) acts as a nucleophile," we always mean

Circle all possible products for the reaction: ​

Give the two organic products of the reaction. (Ignore stereochemistry.)

Consider this reaction: + $\mathrm { Na } ^ { + } \mathrm { MeO } ^ { - } \underset { \mathrm { MeOH } } { \longrightarrow } \text { substitution and } \beta \text {-elimination products }$ Draw the structures of the two -elimination products that can be formed in this reaction.

Rank the starting materials in terms of their rate of product formation in a reaction with sodium fluoride in dimethylformamide (1 being the fastest and 5 being the slowest). (Dimethylformamide (DMF) is a polar aprotic solvent.) $\mathrm { Na } ^ { + } \mathrm { F } ^ { - } + \mathrm { R } - \mathrm { X } \stackrel { \mathrm { DMF } } { \longrightarrow } \mathrm { R } - \mathrm { F } + \mathrm { Na } ^ { + } \mathrm { X } ^ { - }$ ​

Under what conditions would the reaction be most likely to proceed to the product shown at a reasonable rate? (Select one.)

What are the two products that form during an E2 reaction on (1-bromoethyl)-cyclohexane?

(a) Provide the structure of the missing starting material. (b) Then, assuming the reaction occurs via an S_N2 mechanism, provide the rate law using the appropriate concentration terms.

According to the rate law for the S_N2 reaction, doubling the nucleophile concentration (without changing the concentration of the electrophilic compound) should (select one)