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Problem 7
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
Problem 8a
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 (found in the citric acid cycle, Section 21.8) <IMAGE>
Problem 8b
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 (found in glycolysis, Section 22.3) <IMAGE>
Problem 10a
Are the pairs of compounds shown below the same molecule, isomers, or different molecules? <IMAGE>
Problem 12.37
If one compound has the formula C₅H₁₀ and another has the formula C₄H₁₀ are the two compounds isomers? Explain.
Problem 12.43a
Write condensed structures for the following molecular formulas. More than one isomer will be required for each.
Isomers of C₈H₁₈ that contain two methyl groups and a longest chain of 4 carbons
Problem 12.44b
How many straight-chain isomers can you write that fit the following descriptions? See Worked Example 12.12 for guidance.
Amines (―NH₂) with a longest chain of 7 carbons
Problem 12.45c
How many isomers can you write that fit the following descriptions? See Worked Example 12.12 for guidance.
Alcohols (―OH) formed from 2-methylhexane
Problem 12.46a
Which of the following pairs of structures are identical, which are isomers, and which are unrelated? <IMAGE>
Problem 12.51
Give IUPAC names for the five isomers with the formula C₆H₁₄.
Problem 12.59
Draw the structural formulas and name all cyclic isomers with the formula C5H10.
Problem 13.11
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.
Problem 13.13a
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
Problem 13.2
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
Problem 13.23
Reaction of Br2 and FeBr3 with phenol can lead to three possible substitution products. Show the structure of each and name them.
Problem 13.28
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.
Problem 13.34a
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)
Problem 13.34b
Write structural formulas for compounds that meet the following descriptions:
b. An alkyne with 5 carbons total (three possibilities)
Problem 13.35a
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
Problem 13.35b
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.
Problem 13.38
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
Problem 13.4
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)
Problem 13.40
Seven alkynes have the formula C₆H₁₀. Draw them using line structures.
Problem 13.54
If 2-methyl-2-pentene were converted into 1-hexene, what kind of reaction would that be?
Problem 13.57a
Identify the type of reaction for the following:
a. <IMAGE>
b. <IMAGE>
Problem 13.60
What alkene could you use to make the following products? Draw the structure of the alkene, and tell what other reagent is also required for the reaction to occur.
a. <IMAGE>
Problem 13.60c
What alkene could you use to make the following products? Draw the structure of the alkene, and tell what other reagent is also required for the reaction to occur.
c. <IMAGE>
Problem 13.60d
What alkene could you use to make the following products? Draw the structure of the alkene, and tell what other reagent is also required for the reaction to occur.
d. <IMAGE>
Problem 13.62
1-Pentyne reacts with HBr in a 1:1 molar ratio to yield two different addition products, both being bromopentenes and having the chemical formula C₅H₉Br . Draw the structures of two possible products.
Problem 13.67
Aromatic compounds do not normally react with hydrogen in the presence of a palladium catalyst but will if very high pressures (200 atm) and high temperatures are used. Under these conditions, toluene adds three molecules of H2 to give an alkane addition product. What is a likely structure for the product?
