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Problem Set No. 1 1. Sort the following compounds according to their pKa-values: 2. Provide the products and calculate the K

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Modern Synthetic Methods Name:

D. Tyler McQuade

Problem Set No. 1

1. Sort the following compounds according to their pKa-values:

2. Provide the products and calculate the Keq for the following reaction and determine the free energy. Indicate whether the reaction is reversible or not. (see https://webspace.utexas.edu/ccl524/CH318N/pKa_Keq.pdf) and (remember G = -RTLnKeq).

(2)

3. a) Give a mechanistic description of the formation of an organolithium species from lithium metal and provide the term used to describe this process.

Direct Approach or Direct Synthesis

b) What figure of merit can be used to predict if a solvent will be compatible with n- BuLi. Give examples of solvents compatible and incompatible.

pKa of most acidic proton on the solvent or whether or not the solvent is electrophilic.

Compatible solvents: diethyl ether, hydrocarbons (pentane, hexane, cyclohexane, heptane).

Stability at low temperature: THF, Toluene

Incompatible: DMF, CH3CN, CHCl3, CH2Cl2, EtOAc, EtOH, MeOH, Acetone, DMSO.

The students only need to give two examples of compatible and incompatible

c) Above -20oC n-BuLi reacts with THF (tetrahydrofuran) provide a detailed reaction mechanism and draw all products after hydrolysis.

Referenzen

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