4. Alkanes and Cycloalkanes

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>

Draw the most energetic Newman Projection of CH₃CH(C₆H₅)CH₃

Given the following structures, show the Newman projection that would result from looking down the indicated bond in the direction shown. [Orient yourself as if you were the eyeball looking down the bond. Some of the examples have been partially completed for you to fill in the rest.]

(l) <IMAGE>

Using Newman projections, draw the most stable conformer for each of the following:

c. 3,3-dimethylhexane, viewed along the C-3---C-4 bond

Given the first Newman projection and the direction and degree of rotation, fill in the resulting Newman projection. [One substituent has been labeled for you.]

(d)

For each of the following structures, which staggered Newman projection skeleton from Assessment 3.51 should you draw first to show what is seen when looking down the indicated bond?

(d) <IMAGE>

Given the first Newman projection and the direction and degree of rotation, fill in the resulting Newman projection. [One substituent has been labeled for you.]

(l)

Draw Newman projections of the following molecules viewed from the direction of the blue arrows.

(a)

Given the first Newman projection and the direction and degree of rotation, fill in the resulting Newman projection. [One substituent has been labeled for you.]

(a)

Convert each Newman projection to the equivalent line–angle formula, and assign the IUPAC name.

(a)

(b)

Convert the following Newman projections to skeletal structures and name them.

a.

b.

Given the following structures, show the Newman projection that would result from looking down the indicated bond in the direction shown. [Orient yourself as if you were the eyeball looking down the bond. Some of the examples have been partially completed for you to fill in the rest.]

(i) <IMAGE>

For the following molecule, draw the Newman projection (around the 2,3-bond) with a dihedral angle of 180° between the bromine and hydrogen.

Draw Newman projections along the C3―C4 bond to show the most stable and least stable conformations of 3-ethyl-2,4,4-trimethylheptane.

Use a Newman projection about the indicated bond to draw the most stable conformer for each compound.

b. 3,3-dimethylhexane about the C3―C4 bond