Draw both condensed and line structures corresponding to the following IUPAC names:

a. 3-Methyl-1-heptene

b. 4,4-Dimethyl-2-pentyne

c. 2-Methyl-3-hexene

d. 1,3,3-Trimethylcyclohexene

Which of the following substances exist as can cis–trans isomers? Draw both isomers for those that do.

a. 2,3-Dimethyl-2-pentene (condensed structures only)

b. 2-Methyl-2-hexene (both condensed and line structures)

c. 2-Hexene (line structures only)

Classify the following reactions as an addition, elimination, or substitution:

a. CH₃Br + NaOH → CH₃OH + NaBr

b. H₂C═CH₂ + HCl → CH₃CH₂Cl

c. CH₃CH₂Br → H₂C═CH₂ + HBr

Many biological transformations can be simply classified as additions, eliminations, or substitutions. How would you classify the following reactions?

a. Fumaric acid to malic acid

Many biological transformations can be simply classified as additions, eliminations, or substitutions. How would you classify the following reactions?

b. 2-Phosphoglyceric acid to phosphoenolpyruvic acid

Draw all possible products formed when 2-methyl-2-butene undergoes addition with HCl. Label them as being either the major or the minor product.

In the following addition reactions, are the given alkyl halides obtained as the major products? Give a reason for your answer.

a. 3-Chloro-3-ethylpentane from addition of HCl to 3-ethyl-2-pentene

Draw the structures of the two different alkenes from which 3-methyl-3-pentanol, shown in the margin, can be made. Draw them in both condensed and line format.

The structure of vinyl acetate is shown below (the partial structure H₂C=CH-is known as a vinyl group). When polymerized it produces poly(vinyl acetate), a polymer used for the springy soles in running shoes. Draw the structure of the polymer obtained if three vinyl acetate units underwent polymerization.

Draw structures corresponding to the following names (refer to Table 13.2 if necessary):

a. m-Chloronitrobenzene

b. o-Nitrotoluene

c. p-Methylaniline

d. p-Nitrophenol

Reaction of Br₂ and FeBr₃ with phenol can lead to three possible substitution products. Show the structure of each and name them.

Draw the product from reaction of the following substances with (1) Br₂ and FeBr₃ and (2) SO₃ and H₂SO₄ catalyst (red=O):

(a) <IMAGE>

(b) <IMAGE>

Alkynes undergo hydrogenation to give alkanes, just as alkenes do. Draw and name the products that would result from hydrogenation of the alkynes shown in Problem 13.25.

<IMAGE>

What do the terms saturated and unsaturated mean?

Draw an example of a saturated four carbon compound and an unsaturated four carbon compound.

What does the term 'aromatic' refer to when discussing organic molecules?

What is resonance and why is it important in aromatic compounds?

What prefixes are used in naming the following?

a. A 1,3-disubstituted benzene

b. A 1,4-disubstituted benzene

Write structural formulas for compounds that meet the following descriptions:

a. A 6-carbon alkene whose longest chain is 4 carbons in length (three possibilities)

Write structural formulas for compounds that meet the following descriptions:

b. An alkyne with 5 carbons total (three possibilities)

Write structural formulas for compounds that meet the following descriptions:

d. A disubstituted benzene with a total of 8 carbons (three possibilities)

Write structural formulas for compounds that meet the following descriptions:

a. An alkene, C₆H₁₂, that cannot have cis–trans isomers and whose longest chain is 5 carbons long

Write structural formulas for compounds that meet the following descriptions:

b. An alkene with a chemical formula of C₁₀H₁₂, that has cis–trans isomers and contains a benzene ring.

Draw structures corresponding to the following IUPAC names:

a. trans-2-Pentene

b. trans-3,4-Dimethyl-3-hexene

c. 2-Methyl-1,3-butadiene

d. trans-3-Heptene

Seven alkynes have the formula C₆H₁₀. Draw them using line structures.

Draw and name all phenols with the formula C₇H₈O .

When ethylbenzene is reacted with nitric acid, three possible benzenes containing both a nitro group and an ethyl group are obtained. Draw and name them.

What is the difference between a substitution reaction and an addition reaction?

If 2-methyl-2-pentene were converted into 1-hexene, what kind of reaction would that be?

If bromocyclohexane were converted into cyclohexene, what kind of reaction would that be?