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4. Alkanes and Cycloalkanes

Drawing Newman Projections

4. Alkanes and Cycloalkanes

Drawing Newman Projections

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Introduction to Drawing Newman Projections

Introduction to Drawing Newman Projections

Johnny Betancourt

Step 1 to Drawing Newman Projections

Step 1 to Drawing Newman Projections

Johnny Betancourt

Step 2 to Drawing Newman Projections

Step 2 to Drawing Newman Projections

Johnny Betancourt

Step 3 to Drawing Newman Projections

Step 3 to Drawing Newman Projections

Johnny Betancourt

Step 4 to Drawing Newman Projections

Step 4 to Drawing Newman Projections

Johnny Betancourt

Step 5 to Drawing Newman Projections

Step 5 to Drawing Newman Projections

Johnny Betancourt

Step 6 to Drawing Newman Projections

Step 6 to Drawing Newman Projections

Johnny Betancourt

Showing 7 of 7 videos

Practice this topic

Multiple Choice

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

Multiple Choice

Draw the most stable Newman Projection of CH₃CH₂ CH₂OH through the C2 – C1 bond.

Multiple Choice

Which line-angle structure matches the Newman projection, when looking from the right?

Textbook Question

Use a Newman projection about the indicated bond to draw the most stable conformer for each compound. a. 3-methylpentane about the C2―C3 bond

Textbook Question

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

Textbook Question

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

Textbook Question

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

Textbook Question

Draw a Newman projection, similar to [FIGURE 3-25}

down the C1—C6 bond in the equatorial conformation of methylcyclohexane. Show that the equatorial methyl group is also anti to C5. (Using your models will help.)

Textbook Question

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

Textbook Question

Draw Newman projections of the following molecules viewed from the direction of the blue arrows. a. [SOLVED]

Textbook Question

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

Textbook Question

a. Draw all the staggered and eclipsed conformers that result from rotation about the C-2-C-3 bond of pentane.

Textbook Question

Using Newman projections, draw the most stable conformer for each of the following: b. 3-methylhexane, viewed along the C-3-C-4 bond

Textbook Question

Using Newman projections, draw the most stable conformer for each of the following: a. 3-methylpentane, viewed along the C-2-C-3 bond

Textbook Question

b. Draw a potential-energy diagram for rotation about the C-2-C-3 bond of pentane through 360°, starting with the least stable conformer.

Textbook Question

For rotation about the C-3-C-4 bond of 2-methylhexane, do the following: a. Draw the Newman projection of the most stable conformer. b. Draw the Newman projection of the least stable conformer.

Textbook Question

c. Draw Newman projections of the two conformers of the trans isomer. d. Which of the conformers predominates at equilibrium?

Textbook Question

(••) 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.] [On these last three, you need to use the line angle drawings without hydrogens or carbons shown.] (i)

Textbook Question

(••) 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.] [On these last three, you need to use the line angle drawings without hydrogens or carbons shown.] (h)

Textbook Question

Using the Newman projections shown, draw each molecule in its line-angle drawing with all hydrogens and substituents shown. [Carbon b is behind carbon a in these structures.] Wedges and dashes should be used to indicate whether a substituent is coming out of, or going into, the plane of the page. [Your answers to these will look like the molecules in Assessment 3.21.] (b)

Textbook Question

Using the Newman projections shown, draw each molecule in its line-angle drawing with all hydrogens and substituents shown. [Carbon b is behind carbon a in these structures.] Wedges and dashes should be used to indicate whether a substituent is coming out of, or going into, the plane of the page. [Your answers to these will look like the molecules in Assessment 3.21.] (d)

Textbook Question

(•) 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)

Textbook Question

(•) 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)

Textbook Question

(•) 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)

Textbook Question

(•) 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)

Textbook Question

(••) 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)

Textbook Question

(••) 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.] [On these last three, you need to use the line angle drawings without hydrogens or carbons shown.] (j)

Textbook Question

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

Textbook Question

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

Textbook Question

For each molecule, draw the Newman projection you would observe if you looked down the Cₐ - Cᵦ bond in the direction indicated.

(d) <IMAGE>

Textbook Question

(••) 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>

Textbook Question

(•••) 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>

Textbook Question

(••) 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>

Textbook Question

Is each of the following a cis isomer or a trans isomer?

d. <IMAGE>

e. <IMAGE>

f. <IMAGE>

Textbook Question

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

c. <IMAGE>

d. <IMAGE>

Textbook Question

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

Textbook Question

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

Textbook Question

Conformational studies on ethane-1,2-diol (HOCH2—CH2OH) have shown the most stable conformation about the central C―C bond to be the gauche conformation, which is 9.6 kJ/mol (2.3 kcal/mol) more stable than the anti conformation.

Draw Newman projections of these conformers, and explain this curious result.

Textbook Question

b. Draw the conformer that is present in greatest concentration.

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