For each structure shown, draw the two chair conformations and choose which is most stable. Be sure that your second chair is the flipped version of the first. [Make sure that wedged substituents are up in the chair, regardless of whether up is equatorial or axial.]

(e)

For each structure shown, draw the two chair conformations and choose which is most stable. Be sure that your second chair is the flipped version of the first. [Make sure that wedged substituents are up in the chair, regardless of whether up is equatorial or axial.]

(g)

Calculate the energy difference between each pair of conformations shown by drawing and comparing Newman projections down the indicated bonds in each.

(b)

In contrast to ethane and other alkanes studied in this chapter, there is no free rotation around any bonds in cyclopentane (shown below). Why?

Looking ahead In Chapter 5, we explain that the equilibrium constant (K_eq) for a reaction can be calculated based on the difference in energy between reactants and products, according to the following equation:

$K_{eq}=e^{-\frac{\Delta E}{RT}}$

Using this equation, calculate the equilibrium constant for the 'reaction' shown. [For the rest of the book, if not otherwise specified, assume room temperature (298K).]

The normal C(sp³)–C(sp³) bond length is 1.54 Å. The normal bond angle for an sp³-hybridized carbon is 109.5°. The following molecule experiences large deviations from these normal values. Explain these deviations. [Molecular models would be helpful here.]

In Chapter 5, we introduce reaction coordinate diagrams as a plot of potential energy versus the progress of a reaction. Consider the reaction coordinate diagram drawn for the 'reaction' of conformation A becoming conformation B. Which structure is present at the top of the hill?

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Correct the following incorrect names using standard IUPAC nomenclature. [Draw a compound that corresponds to the incorrect name, and then rename it.]

(a) 4-methylhexane

Correct the following incorrect names using standard IUPAC nomenclature. [Draw a compound that corresponds to the incorrect name, and then rename it.]

(b) 1,5-dimethylcyclohexane

Correct the following incorrect names using standard IUPAC nomenclature. [Draw a compound that corresponds to the incorrect name, and then rename it.]

(c) 6-ethyl-3-methyloctane

Correct the following incorrect names using standard IUPAC nomenclature. [Draw a compound that corresponds to the incorrect name, and then rename it.]

(d) 4-butyldecane

Correct the following incorrect names using standard IUPAC nomenclature. [Draw a compound that corresponds to the incorrect name, and then rename it.]

(e) 2,6-diethyl-1-methylcycloheptane

Identify the mistakes contained within the following structures.

(a)

Despite methylcyclohexane (98.2 amu) having a higher molecular weight than toluene (92.1 amu), toluene melts at a higher temperature. Why? [Think about how the molecules can interact with each other based on their shape.]

Ionic compounds like sodium acetate have a high melting point. Despite this, they are highly soluble in water. Why?

Identify the functional groups in each of the following molecules. [The number of functional groups has been given to assist you.]

(a) [Three]

Identify the functional groups in each of the following molecules. [The number of functional groups has been given to assist you.]

(b) [Two]

Identify the functional groups in each of the following molecules. [The number of functional groups has been given to assist you.]

(c) [Three]

Identify the functional groups in each of the following molecules. [The number of functional groups has been given to assist you.]

(d) [Two]