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Chapter 4: Q15. (page 146)

Which of the following is (are) possible Newman projections for 2-methylpentane?

Short Answer

Expert verified

The possible Newman projections for 2-methylpentane are A and B.

Step by step solution

01

Step 1. Newman projection

Newman's projection involves the representation of alkane with the help of dots and circles. Two carbon atoms are required in this projection.

02

Step 2. Explanation for possible Newman projections

The given compound is 2-methylpentane. The possible Newman projections for 2-methylpentane are mentioned below:

Staggered conformation

03

Step 3. Explanation for wrong projection

The compound C is the conformation of 3-methylpentane as shown below:

Compound C

Thus, the possible Newman projections for 2-methylpentane are A and B.

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Most popular questions from this chapter

Question: Consider the substituted cyclohexane shown in the ball-and-stick model.

  1. Label the substituents on C1, C2, and C4 as axial or equatorial.
  2. Are the substituents on C1 and C2 cis or trans to each other?
  3. Are the substituents on C2 and C4 cis or trans to each other?
  4. Draw the second possible conformation in the chair form, and classify it as more stable or less stable than the conformation shown in the three-dimensional model.

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: a. Using Newman projections, draw all staggered and eclipsed conformations that result from rotation around the bond highlighted in pink in each molecule;

b. draw a graph of energy versus dihedral angle for rotation around this bond.

Question: Draw the two possible chair conformations for cis-1,3-dimethylcyclohexane. Which conformation, if either, is more stable?

Question: Answer the following questions about compounds A–D.

a. How are the compounds in each pair related? Choose from constitutional isomers, stereoisomers, or identical molecules: A and B; A and C; B and D.

b. Label each compound as a cis or trans isomer.

c. Draw B as a hexagon with wedges and dashed wedges to show the stereochemistry of substituents.

d. Draw a stereoisomer of A as a hexagon using wedges and dashed wedges to show the orientation of substituents.
See all solutions

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