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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’s 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° 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:

Totalstrainenergy=3×3.8kJmol=11.4kJmol

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Most popular questions from this chapter

Identify the carbon atoms in the following molecules as primary, secondary, tertiary, or quaternary:

C)

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

Question: The barrier to rotation about the C-C bond in bromoethane is 15 kJ/mol (3.6 kcal/mol).

(a) What energy value can you assign to an H←→Br eclipsing interaction?

(b) Construct a quantitative diagram of potential energy versus bond rotation for bromoethane.

Locate and identify the functional groups in the following molecules.

Draw compounds that contain the following:

  1. A primary alcohol
  2. A tertiary Nitrile
  3. A secondary Thiol
  4. Both primary and secondary alcohols
  5. An isopropyl group
  6. A quaternary carbon
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