Organic Chemistry

108 CHAPTER 2 An Introduction to Organic Compounds

b. Which takes up more space, the lone-pair electrons or the methyl group?

59. How many ethers have the molecular formula Give the structural formula and systematic name for each. What are their
    common names?


60. Draw the most stable conformer of the following molecule:


61. Give the systematic name for each of the following compounds:
    a. d.

b. e.

c.

62. Calculate the energy difference between the two chair conformers of trans-1,2-dimethylcyclohexane.


63. The most stable form of glucose (blood sugar) is a six-membered ring in a chair conformation with its five substituents all in
    equatorial positions. Draw the most stable form of glucose by putting the OH groups on the appropriate bonds in the chair
    conformer.


64. Explain the following facts:
    a. 1-Hexanol has a higher boiling point than 3-hexanol.
    b. Diethyl ether has very limited solubility in water, but tetrahydrofuran is essentially completely soluble.


65. One of the chair conformers of 1,3-dimethylcyclohexane has been found to be 5.4 kcal mol (or 23 kJ mol) less stable than the
    other. How much steric strain does a 1,3-diaxial interaction between two methyl groups introduce into the conformer?


66. Calculate the amount of steric strain in each of the chair conformers of 1,1,3-trimethylcyclohexane. Which conformer would
    predominate at equilibrium?

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O

tetrahydrofuran

CH 2 OH

CH 2 OH

OH

HO OH

HO

O O

glucose

CH 3 CHCHCH 2 CH 2 CH 2 Cl

Cl

CH 2 CH 3

CH 3 CH 2 CH 2 CH 2 CH 2 CHCH 2 CHCH 2 CH 3

CH 2

CH 3 CCH 3

CH 2 CH 3

CH 2 CH 3

CH 3 CH 2 CHCH 2 CHCH 2 CH 3

CHCH 3

CH 3

CH 3

CH 3 CH 2 CH 2 CH 2 CHCH 2 CH 2 CH 2 CH 3

CH 3 CCH 2 CH 3

CH 3

CH 3 CH 2 CHCH 2 CH 2 CHCH 3

NHCH 3 CH 3

CH 3

H 3 C CH 3

C 5 H 12 O?

N

N-methylpiperidine

CH 3

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