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Chapter 3: Q18P (page 86)

Draw a Newman projection along the C2-C3 bond of the following conformation of 2,3-dimethylbutane, and calculate a total strain energy:

Short Answer

Expert verified

The total strain energy is 11.4 kJ mol.

Step by step solution

01

Newman Projection 

Newman projections are important for understanding alkane stereochemistry. A chemical bond鈥檚 conformation from front part to back part can be visualized using Newman projection.

02

Drawing the Newman projection and calculating the total strain energy

The confirmation given here is a staggered conformation and the hydrogens on carbons 2 and 3 are60掳 apart.

The Newman projection exhibits three gauche interactions. Each of the interactions have an energy of 3.8 kJ/mol.

Newman projection of the molecule

The total strain energy of the molecule can be given as:

罢辞迟补濒蝉迟谤补颈苍别苍别谤驳测=3脳3.8kJmol=11.4kJmol

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Most popular questions from this chapter

We鈥檒l see in the next chapter that there are two isomeric substances, both named 1,2-dimethylcyclohexane. Explain.

Increased substitution around a bond leads to increased strain. Take the four substituted butanes listed below, for example. For each compound, sight along the C2鈥揅3 bond and draw Newman projections of the most stable and least stable conformations. Use the data in Table 3-5 to assign strain-energy values to each conformation. Which of the eight conformations is most strained? Which is least strained?

(a) 2-Methylbutane

(b) 2,2-Dimethylbutane

(c) 2,3-Dimethylbutane

(d) 2,2,3-Trimethylbutane

Give IUPAC names for the following alkanes, and convert each drawing

into a skeletal structure.

Draw structures corresponding to the following IUPAC names:

(c) 2,2-Dimethyl-4-propyloctane

Sight along the C2-C1 bond of 2-methylpropane (isobutane).

(d) Assign relative values to the maxima and minima in your graph, given that

An eclipsing interaction costs 4.0 kJ/mol and an H鈫�CH3eclipsing

Interaction costs 6.0 kJ/mol.
See all solutions

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