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Question: Consider rotation around the carbon-carbon bond in 1,2-dichloroethane (ClCH2CH2Cl).

a.Using Newman projections, draw all of the staggered and eclipsed conformations that result from rotation around this bond.

b. Graph energy versus dihedral angle for rotation around this bond.

Short Answer

Expert verified

Answer

a.

b.

Step by step solution

01

Step 1:Stability and energy

The energy of the conformation is based upon the repulsion of the bulky groups. The more the repulsion, the more will be energy.

Also, the conformation will be unstable.

02

Newman projection

The given compound is 1,2-dichloroethane. The Newman projection for the given compound is shown below:

Newman projection for 1,2-dichloroethane

03

Explanation

a.

By fixing the front carbon, the back carbon is rotated by 600. As a result, three staggered and three eclipsed conformations are produced as shown below:

Conformation of 1,2-dichloroethane

b.

The relation between the positions of the bulky groups with energy and stability is mentioned below:

  • When the two bulkier groups (chlorine) are anti or opposite to each other, the energy of the conformation is the minimum, and it is stable.
  • When the two bulkier groups (chlorine) are at 1200, the energy of the conformation is larger as above, and it is slightly stable.
  • When the two bulkier groups (chlorine) are at 600, the energy of the conformation is the largest as the above two conformations, and it is unstable.

The graph between energy and dihedral angle is shown below:

Graph representing energy and dihedral angle

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Most popular questions from this chapter

Question: Draw the five constitutional isomers having molecular formula C6H14.

Question: Answer the following questions about compound A, which contains a -CH3group and OH group bonded to the carbon skeleton that consists of three six-membered rings in the conformation shown.

a. Are the -CH3and OH groups oriented cis or trans to each other?

b. Is a substituent on localid="1648626189057" Cathat is cis to the CH3 group located in the axial or equatorial position?

c. Is an equatorial Br at Cboriented cis or trans to the OH group?

d. Is the H atom on Cclocated cis or trans to the OH group?

e. Is a substituent on Cdthat is trans to the OH group located in the axial or equatorial position?

Question: When two six-membered rings share a C-C bond, this bicyclic system is called decalin. There are two possible arrangements: trans-decalin having two hydrogen atoms at the ring fusion on opposite sides of the rings, and cis-decalin having the two hydrogens at the ring fusion on the same side.

  1. Draw trans- and cis-decalin using the chair form for the cyclohexane rings.
  2. The trans isomer is more stable. Explain why.

Question: For each compound drawn below:

a. Label each OH, Br, andCH3group as axial or equatorial.

b. Classify each conformation as cis or trans.

c. Translate each structure into a representation with a hexagon for the six-membered ring, and wedges and dashed wedges for groups above and below the ring.

d. Draw the second possible chair conformation for each compound.

Draw the staggered and eclipsed conformations that result from rotation around the C-C bond inCH3-CH2Br.

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