Chapter 10

Why is the organic chemical industry referred to as the petrochemical industry?

What products are produced by the petrochemical industry?

What is the difference between catalytic cracking and catalytic reforming?

Explain how the octane number of a gasoline is determined.

What is the difference between oxygenated gasoline and reformulated gasoline? Why are they being produced?

Table 10.1 lists several compounds with octane numbers above 100 and one compound with an octane number below zero. Explain why such values are possible.

Explain why methanol has a lower boiling point \(\left(65.0^{\circ} \mathrm{C}\right)\) than water \(\left(100^{\circ} \mathrm{C}\right)\)

Give two reasons why ethylene glycol has a higher boiling point than ethanol.

What is the major difference between crude oil and coal as a source of hydrocarbons?

Write the structural formula of a representative compound for each of these classes of organic compounds: alcohols, aldehydes, ketones, carboxylic acids, esters, and amines.

Describe the structural feature a molecule must have to undergo addition polymerization.

What feature do all condensation polymerization reactions have in common?

Give examples of (a) a synthetic addition polymer, (b) a synthetic condensation polymer, and (c) a natural addition polymer.

Discuss which two plastics are currently being recycled the most successfully, and give examples of some products being made from these recycled plastics.

What is the difference between the formation of an addition polymer and a condensation polymer?

What are petroleum fractions? What process is used to produce them?

Explain what is meant by this statement: "All gasolines are highly volatile."

What would be the advantage of removing the higheroctane components such as aromatics and alkenes from oxygenated gasolines?

Describe the major change that has occurred over the past few years in the source of natural gas in the United States.

Describe how hydraulic fracturing differs from conventionally drilled oil and gas wells.

Do polar compounds appear earlier or later on a chromatogram when a nonpolar stationary phase is used? Explain your answer.

If you were to analyze an oxygenated gasoline using GC, would you use a less polar or more polar stationary phase than the one used for unoxygenated gasoline?

Give an example of (a) a primary alcohol, (b) a secondary alcohol, and (c) a tertiary alcohol. Draw Lewis structures for each example.

Explain what oxidation of organic compounds usually involves. What is meant by reduction of organic compounds?

Draw the structures of the first two oxidation products of each of these alcohols. (a) \(\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{OH}\) (b) \(\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{CH}_{2} \mathrm{CH}_{2} \mathrm{OH}\)

What is the percentage of ethanol in 90 -proof vodka?

Explain how the common name grain alcohol for ethanol came about.

What is denatured alcohol? Why is it made?

Many biological molecules, including steroids and carbohydrates, contain many \(-\) OH groups. What need might biological systems have for this particular functional group?

What kind of electromagnetic radiation is used in nuclear magnetic resonance (NMR)?

Using structural formulas, write the equation for the formation of a triglyceride formed by the reaction of \(1 \mathrm{~mol}\) glycerol with \(2 \mathrm{~mol}\) stearic acid and \(1 \mathrm{~mol}\) oleic acid.

For the three fatty acids given below, (a) classify each as saturated or mono-, di-, or polyunsaturated. (b) write a balanced equation for formation of a triglyceride that incorporates all three. (i) arachidonic acid $$ \mathrm{CH}_{3}-\left(\mathrm{CH}_{2}\right)_{4}-\left(\mathrm{CH}=\mathrm{CH}-\mathrm{CH}_{2}\right)_{4}-\left(\mathrm{CH}_{2}\right)_{2}-\mathrm{COOH} $$ (ii) nervonic acid CCCCC(CC(C)C)CC(OC)C(=O)O (iii) myristic acid CCC(C)C(=O)O

Melissyl cerotate has this structural formula: CCCC(=O)OCC (a) Identify the type of compound melissyl cerotate is. (b) Write the structural formulas of the compounds produced by the hydrolysis of melissyl cerotate.

Explain why the boiling points for carboxylic acids are higher than those for alcohols with comparable numbers of electrons.

Write the structural formula of the ester that can be formed from each reaction. (a) \(\mathrm{CH}_{3} \mathrm{COOH}+\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{OH}\) (b) \(\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{COOH}+\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{CH}_{2} \mathrm{OH}\) (c) \(\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{COOH}+\mathrm{CH}_{3} \mathrm{OH}\)

Write the structural formula for the ester that can be produced by each reaction. (a) Formic acid \(+\) methanol (b) Butyric acid \(+\) ethanol (c) Acetic acid +1 -butanol (d) Propanoic acid +2 -propanol

Explain why carboxylic acids are more soluble in water than are esters with the same number of electrons.

Explain why esters have lower boiling points than carboxylic acids with the same number of electrons.

Give two examples of thermoplastics. What are the properties of thermoplastics when heated and cooled?

Give two examples of everyday items that are thermosetting plastics. What are the properties of thermosetting plastics when heated and cooled?

Draw the structure of the repeating unit in a polymer in which the monomer is (a) 1 -butene. (b) 1,1 -dichloroethylene. (c) vinyl acetate.

What is the principal structural difference between lowdensity and high- density polyethylene? Is polyethylene an addition or a condensation polymer?

Write the structural formula of four units of the polymer made from the reaction of \(\mathrm{H}_{2} \mathrm{~N}-\left(\mathrm{CH}_{2}\right)_{4}-\mathrm{NH}_{2}\) and \(\mathrm{HOOCCOOH}\). Indicate the repeating unit of the polymer.

What are the two monomers used to make SBR?

Which functional groups must be present in a single monomer to form a polyester?

Name one important polyester polymer and its uses.

Polyamides are made by condensing which functional groups? Name the most common example of this class of synthetic polymers.

Orlon has this polymeric chain structure: CCC(C)CC(C)CC(C)C(C)C What is the monomer from which this structure can be made?

How many ethylene units are in a polyethylene molecule that has a molecular weight of approximately \(42,000 ?\)

Write a structural formula for the repeating unit of each polymer. (a) Natural rubber (poly-cis-isoprene) (b) Neoprene (c) Polybutadiene