Organic Chemistry · free preview

Chapter 4: Review and Practice

Cyclic molecules are so commonly encountered throughout organic and biological chemistry that it’s important to understand the consequences of their cyclic structures. Thus, we’ve taken a close look at cyclic structures in this chapter.

1. Cyclic molecules are so commonly encountered throughout orga

Cyclic molecules are so commonly encountered throughout orga

2. Cyclohexane is strain-free because it adopts a puckered chai

Cyclohexane is strain-free because it adopts a puckered chai

3. Chemistry Matters — Molecular Mechanics

Chemistry Matters — Molecular Mechanics

4. After calculating a total strain energy for the starting geo

After calculating a total strain energy for the starting geo

5. Additional Problems

Additional Problems

6. Problem 4-26 Glucose exists in two forms having a 36:64 rati

Problem 4-26 Glucose exists in two forms having a 36:64 rati

7. Problem 4-30 (a) cis-1,3-Dibromocyclohexane and trans-1,4-di

Problem 4-30 (a) cis-1,3-Dibromocyclohexane and trans-1,4-di

8. Problem 4-34 Hydrocortisone, a naturally occurring hormone p

Problem 4-34 Hydrocortisone, a naturally occurring hormone p

9. Problem 4-38 Which is more stable, a 1,4-trans disubstituted

Problem 4-38 Which is more stable, a 1,4-trans disubstituted

10. Problem 4-42 Draw the two chair conformations of cis-1-chlor

Problem 4-42 Draw the two chair conformations of cis-1-chlor

11. Problem 4-46 There are four cis–trans isomers of menthol (Pr

Problem 4-46 There are four cis–trans isomers of menthol (Pr

12. Problem 4-50 One of the two chair structures of cis-1-chloro

Problem 4-50 One of the two chair structures of cis-1-chloro

13. Problem 4-54 As mentioned in Problem 3-53, the statin drugs,

Problem 4-54 As mentioned in Problem 3-53, the statin drugs,

14. Problem 4-58 (a) Substituent up at C3 ubstituent up at C3 (b

Problem 4-58 (a) Substituent up at C3 ubstituent up at C3 (b

15. Problem 4-62 Alcohols undergo an oxidation reaction to yield

Problem 4-62 Alcohols undergo an oxidation reaction to yield

16. Key Terms

Key Terms

17. - cis–trans isomers - conformational analysis - cycloalkanes

  • cis–trans isomers - conformational analysis - cycloalkanes

18. - Equatorial position (cyclohexane) - polycyclic molecule -

  • Equatorial position (cyclohexane) - polycyclic molecule -

19. - steric strain - torsional strain - twist-boat conformation

  • steric strain - torsional strain - twist-boat conformation

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