Name the following alkanes using the IUPAC system of nomenclature. [Each molecule exemplifies one of the nomenclature rules in Tables 3.7 and 3.8.]

(k) rule 6

Name the following alkanes using the IUPAC system of nomenclature. [Each molecule exemplifies one of the nomenclature rules in Tables 3.7 and 3.8.]

(n) rule 7

When we begin studying functional groups, the designation of substitution will be especially important. Label the following bromoalkanes as 1° , 2°, 3°, or 4° based on the carbon to which the bromine is attached.

(b)

When we begin studying reactive intermediates, the designation of substitution will be especially important. Label the following carbocations as 1° , 2°, 3°, or 4° or based on the carbon bearing the positive charge.

(b)

When we begin studying reactive intermediates, the designation of substitution will be especially important. Label the following carbocations as 1° , 2°, 3°, or 4° or based on the carbon bearing the positive charge.

(c)

Name the following alkanes using the common names for branched substituents.

(c)

In Chapter 8, we study the chemistry of alkenes, like ethene. In contrast to ethane, there is no free rotation around the C = C double bond of ethene. Explain this in the context of the molecular orbital picture of ethene.

For each molecule, draw the Newman projection you would observe if you looked down the C_a - C_b bond in the direction indicated.

(d) <IMAGE>

Using the Newman projections shown, draw each molecule in its line-angle drawing with all hydrogens and substituents shown. [Carbon b is behind carbon a in these structures.] Wedges and dashes should be used to indicate whether a substituent is coming out of, or going into, the plane of the page.

(b)

Using the Newman projections shown, draw each molecule in its line-angle drawing with all hydrogens and substituents shown. [Carbon b is behind carbon a in these structures.] Wedges and dashes should be used to indicate whether a substituent is coming out of, or going into, the plane of the page.

(d)

Calculate the dihedral angle (θ) for the conformations shown.

(c)

Calculate the dihedral angle (θ) for the conformations shown.

(a)

Calculate the dihedral angle (θ) for the conformations shown.

(c)

Why is it incorrect to say that the dihedral angle shown is 120° or even 109°?

Calculate the total strain in the eclipsed conformations shown.

(a)

Calculate the total strain in the eclipsed conformations shown.

(b)

Would you expect a CH₃/CH₃ eclipsing interaction to be larger or smaller than 1.3 kcal/mol?

Choose the conformation in each pair that is most stable. If both are equally stable, then write 'no difference.'

(a)

For each of the pairs in Assessment 3.29, which conformation would you expect to be more prominent at equilibrium?

(a)

(b)

(c)

Name the following cycloalkanes using the IUPAC system of nomenclature. [Hint: Each molecule exemplifies one of the cycloalkane nomenclature rules in Table 3.10.]

(a) rule 1

Name the following cycloalkanes using the IUPAC system of nomenclature. [Hint: Each molecule exemplifies one of the cycloalkane nomenclature rules in Table 3.10.]

(c) rule 2

Name the following cycloalkanes using the IUPAC system of nomenclature. [Hint: Each molecule exemplifies one of the cycloalkane nomenclature rules in Table 3.10.]

(e) rule 3

Name the following cycloalkanes using the IUPAC system of nomenclature. [Hint: Each molecule exemplifies one of the cycloalkane nomenclature rules in Table 3.10.]

(g) rule 4

Name the following cycloalkanes using the IUPAC system of nomenclature.

Name the following cycloalkanes using the IUPAC system of nomenclature, being sure to indicate whether they are cis or trans.

(b)

Rank the following compounds in order of their total heat of combustion. These compounds are constitutional isomers, each with a molecular formula of C₆H₁₂.

Draw two chair conformations of the molecules below. Indicate which is most stable.

(a)

Given the following chair conformations, draw each in its planar form as if you were viewing it from above.

(b)

Given the following chair conformations, draw each in its planar form as if you were viewing it from above.

(c)

Given the following chair conformations, draw each in its planar form as if you were viewing it from above.

(d)