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Question: Label each compound as cis or trans. Then draw the second chair conformation.

a.

b.

c.

Short Answer

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Answer

a.

The given compound is a cis isomer. The structure of the second chair conformation is shown below:

b. The given compound is a trans isomer. The structure of the second chair conformation is shown below:

c. The given compound is a trans isomer. The structure of the second chair conformation is shown below:

Step by step solution

01

Cis and trans isomers

The stereoisomers in which both functional groups are present on the same side of the plane are called cis isomers.

The stereoisomers in which both functional groups are present on the opposite side of the plane are trans-isomers.

02

Identification of cis and trans isomers from the given chair structures

To identify the cis and trans isomers, the positions of the functional groups and the hydrogen atoms have to be categorized as axial and equatorial positions.

The groups on the same side, i.e., axial or equatorial, represent the cis isomers. The groups on the opposite sides are categorized as trans-isomers.

a. The given compound is a cis isomer. Both hydroxyl groups are present at the equatorial positions. The hydroxyl groups are present as down bonds, which mean both are below the plane.

The hydrogen atoms present on the same carbon of the hydroxy groups are positioned upward, i.e., above the plane as shown in the structure below:

Cis cyclohexan-1,3-diol

The second chair conformation can be obtained by the flipping of the ring. It is shown as follows:

Cis cyclohexan-1,3-diol

b. The given compound is a trans isomer. In this compound, both chlorine atoms lie in the same plane.

At one position, as shown in the structure, the chlorine atom is present at the down position, while it is present at the upward position. Both these positions of the chlorine atom are equatorial, as shown in the structures below:

Trans- 1,2-dichloro cyclohexane

The second chair conformation can be obtained by the flipping of the ring as represented in the following structure:

Trans-1,3-dichloro cyclohexane

c. The given compound is a trans isomer. One of the bromine atoms in this compound is present on the up bond, i.e., at the axial position.

The other bromine atom is present on the opposite side as the down bond, i.e., the equatorial position. The structure of the trans compound is shown below:

Trans- 1,3-dibromocyclohexane

The other isomer can be obtained by the flipping of the ring a shown below:

Trans-1,3 dibromo cyclohexane

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Most popular questions from this chapter

Question: The melting points and boiling points of two isomeric alkanes are as follows: CH3(CH2)6CH3, mp=-570C and bp=1260C;(CH3)3CC(CH3)3 , mp=1020C and bp=1060C.

a. Explain why one isomer has a lower melting point but higher boiling point.

b. Explain why there is a small difference in the boiling points of the two compounds but a huge difference in their melting points.

Question: Name each alkane using the ball-and-stick model, and classify each carbon as 10,20,30, or 40.

a.

b.

Question: The torsional energy in propane is 14 kJ/mol (3.4 kcal/mol). Because each H,H eclipsing interaction is worth 4.0 kJ/mol (1.0 kcal/mol) of destabilization, how much is one H, CH3 eclipsing interaction worth in destabilization? (See Section 4.10 for an alternate way to arrive at this value.)

Question: a. Draw the anti and gauche conformations for ethylene glycol (OHCH2CH2OH).

b. Ethylene glycol is unusual in that the gauche conformation is more stable than the anti conformation. Offer an explanation.

Question: Hydrocarbons like benzene are metabolized in the body to arene oxides, which rearrange to form phenols. This is an example of a general process in the body, in which an unwanted compound (benzene) is converted to a more water-soluble derivative called a metabolite, so that it can be excreted more readily from the body.

a. Classify each of these reactions as oxidation, reduction, or neither.

b. Explain why phenol is more water soluble than benzene. This means that phenol dissolves in urine, which is largely water, to a greater extent than benzene.

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