Chapter 22

Explain why carboxylic acids are much stronger acids than alcohols.

The hydrogen at C-1 of 1-butyne is much more acidic than the one at \(\mathrm{C}-1\) in 1 -butene. Explain.

There are two isomers of \(\mathrm{C}_{4} \mathrm{H}_{10}\). Suppose that each isomer is treated with \(\mathrm{Cl}_{2}\) and the products that have the composition \(\mathrm{C}_{4} \mathrm{H}_{8} \mathrm{Cl}_{2}\) are isolated. Find the number of different products that form from each of the original \(\mathrm{C}_{4} \mathrm{H}_{10}\) compounds. Do not consider optical isomerism.

Nitromethane has the formula \(\mathrm{CH}_{3} \mathrm{NO}_{2}\), with the \(\mathrm{N}\) bonded to the \(\mathrm{C}\) and without \(\mathrm{O}-\mathrm{O}\) bonds. Draw its two most important contributing structures. a. What is the hybridization of the C, and how many hybrid orbitals are in the molecule? b. What is the shortest bond? c. Between which two atoms is the strongest bond found? d. Predict whether the HCH bond angles are greater or less than \(109.5^{\circ}\) and justify your prediction.

Free radical fluorination of methane is uncontrollably violent, and free radical iodination of methane is a very poor reaction. Explain these observations in light of bond energies.

Using complete sentences, compare and contrast each of the following. Mention at least two similarities and two differences for each. a. salt and sugar b. methane and 3 -methylheptane c. aldehydes and ketones

The octane rating for gasoline is a measurement of how readily a fuel combusts compared to 2,2,4 -trimethylpentane, an isomer of octane. a. Draw 2,2,4 -trimethylpentane and verify that it is an isomer of octane. b. Draw four other isomers of octane. c. Select one of the isomers and draw it so that it looks differ- ent on the page, but is still the exact same compound. d. Name the isomer you drew in part c. e. Define "isomer" using a complete sentence.

Working individually, have each group member select from the chapter a reaction characteristic of a particular organic functional group. Individually, write out your reaction with one of the following left as a blank: one reactant, one product, or reaction conditions. Pass your reaction to the group member on your right. Have group members fill in the blank of the reaction they receive.