Represent each of the following condensed structural formulas using a line-angle drawing.

(d) CH₃CH₂CH₂CCH₂OH

Represent each of the following condensed structural formulas using a line-angle drawing.

(e) (CH₃)₂CHCH₂CH₂CH₂CH₂CHO

For each molecular formula, represent all constitutional isomers using line-angle drawings.

(b) C₃H₈

For each molecular formula, represent all constitutional isomers using line-angle drawings.

(c) C₄H₁₀

For each molecular formula, represent all constitutional isomers using line-angle drawings.

(e) C₆H₁₄

Draw in all missing lone pairs for the following molecules.

(a)

Draw in all missing lone pairs for the following molecules.

(b)

Draw in all missing lone pairs for the following molecules.

(c)

Draw in all missing lone pairs for the following molecules.

(d)

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)

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)

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.]

(h)

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)

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 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.]

(b) <IMAGE>

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>

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.]

(j) <IMAGE>

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.]

(k) <IMAGE>

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>

For each pair of conformations shown, choose which is most stable. [If both conformations have the same number of gauche interactions, choose the one where the interactions are between smaller groups.]

(e)

For each pair of conformations shown, choose which is most stable. [If both conformations have the same number of gauche interactions, choose the one where the interactions are between smaller groups.]

(f)

Looking down the indicated bond, show the three most stable conformations and choose the one that is most stable. Be sure that the first Newman projection you show is the one you see initially (before rotation). [Why should none of your three Newman projections show eclipsed conformations?]

(b) <IMAGE>

Looking down the indicated bond, show the three most stable conformations and choose the one that is most stable. Be sure that the first Newman projection you show is the one you see initially (before rotation). [Why should none of your three Newman projections show eclipsed conformations?]

(e) <IMAGE>

Using the numbers shown in the chair conformation on the left, label the carbons of the flipped chair on the right. [Assume that the angle through which you view the chair conformation doesn't change.] 

For each chair on the left, place the substituents on the flipped chair. [Recall that the axial/equatorial designation changes from one chair to the next, but the carbon to which the substituent is attached does not.]

(c)

For each chair on the left, place the substituents on the flipped chair. [Recall that the axial/equatorial designation changes from one chair to the next, but the carbon to which the substituent is attached does not.]

(e)

For each chair on the left, place the substituents on the flipped chair. [Recall that the axial/equatorial designation changes from one chair to the next, but the carbon to which the substituent is attached does not.]

(f)

What is the mistake that was made in drawing each of the flipped chairs on the right from the chair on the left? [In these, assume that the angle through which you view the chair conformations doesn't change.]

(a)

For each pair of conformations shown, choose which is most stable. If both are equally stable, then write 'no difference.' [If both conformations have the same number of axial substituents, choose the one with the smallest axial substituents.]

(e)

For each pair of conformations shown, choose which is most stable. If both are equally stable, then write 'no difference.' [If both conformations have the same number of axial substituents, choose the one with the smallest axial substituents.]

(g)