1. PROBLEMS CH 14

2. Learning Check Identify the following compounds as either an aldehyde or ketone. A. CH 3 —CH 2 —CH 2 —COH B. CH 3 —CH 2 —CO—CH 2 —CH 2 —CH 3 C. D.

3. Solution Identify the following compounds as either an aldehyde or ketone. A. CH 3 —CH 2 —CH 2 —COH aldehyde B. CH 3 —CH 2 —CO—CH 2 —CH 2 —CH 3 ketone C.ketone D. aldehyde

4. Learning Check Give the IUPAC name of the following aldehydes. CH 3 —CH—CH 2 —CH 2 —CHO Cl B. A.

5. Solution Give the IUPAC name of the following aldehydes. Step 1 Name the longest carbon chain by replacing the -e in the alkane name with -al. A. pentanal B. benzaldehyde CH 3 —CH—CH 2 —CH 2 —CHO Cl A. B.

6. Solution Give the IUPAC name of the following aldehydes. Step 2 Name and number the substituents by counting the carbonyl group as carbon 1. A. 4-chloro-pentanal B. 2-ethyl- benzaldehyde B. A. 5 4 3 2 1 CH 3 —CH—CH 2 —CH 2 —CHO Cl

7. Classify each as an aldehyde or ketone. Learning Check A. C. B. D.

8. Solution Classify each as an aldehyde or ketone. A. C. B. D. KetoneAldehyde Ketone

9. B. CH 3 ─O─CH 3 A. D.C. Learning Check Classify each as an aldehyde, ketone, alcohol, or ether.

10. Solution B. CH 3 ─O─CH 3 A. D.C. Ketone Ether Aldehyde Alcohol Classify each as an aldehyde, ketone, alcohol, or ether.

11. Learning Check Name each of the following. A.B.C.

12. Solution Name each of the following. A.B.C. Pentanal 3-Chloropropanal 2-Butanone

13. Name the following compounds. Learning Check A. B. C.

14. Solution A. C. 2-Pentanone; methyl propyl ketone B. 3,3-Dimethylbutanal Cyclohexanone Name the following compounds.

15. Learning Check Draw the condensed structural formulas for each of the following. A. 4-Methylpentanal B. 2,3-Dichloropropanal C. 3-Methyl-2-butanone

16. Solution A. 4-Methylpentanal B. 2,3-Dichloropropanal C. 3-Methyl-2-butanone Draw the condensed structural formulas for each of the following.

17. Select the compound in each pair that would have the higher boiling point. Explain. A. An alcohol forms hydrogen bonds. B.There are dipole–dipole attractions between the carbonyl groups. C. Learning Check CH 3 —CH 2 —CH 3 or CH 3 —CH 2 —OH CH 3 —O—CH 3 or

18. Solution Select the compound in each pair that would have the higher boiling point. Explain. Higher Boiling Point Reason A. CH 3 —CH 2 —OH An alcohol forms hydrogen bonds. B.There are dipole–dipole attractions between the carbonyl groups. C. CH 3 —CH 2 —OHAn alcohol forms hydrogen bonds, but an ether does not. An alcohol forms hydrogen bonds. There are dipole–dipole attractions between the carbonyl groups. An alcohol forms hydrogen bonds, but an ether does not CH 3 —CH 2 —OH

19. Learning Check Indicate if each of the following is or is not soluble in water. A. CH 3 —CH 2 —CH 3 B. CH 3 —CH 2 —OH C. D.

20. Solution Indicate if each of the following is or is not soluble in water. A. CH 3 —CH 2 —CH 3 B. CH 3 —CH 2 —OH C. D. not soluble in water soluble in water

21. Learning Check Write the condensed structural formula and the name of the oxidized product when each of the following is mixed with Tollens’ reagent. A. Butanal B. Acetaldehyde C. Ethyl methyl ketone

22. Solution A. Butanal B. Acetaldehyde C. Ethyl methyl ketone Butanoic acid Ethanoic acid, acetic acid Write the condensed structural formula and the name of the oxidized product when each of the following is mixed with Tollens’ reagent. None. Ketones are not oxidized by Tollen’s reagent.

23. Learning Check Predict the product for each of the following reactions. A. + H 2 B. + H 2

24. Solution Predict the product for each of the following reactions. A. + H 2 B. + H 2

25. Learning Check Identify each as a hemiacetal or acetal.

26. Solution Identify each as a hemiacetal or acetal. hemiacetal acetal

27. Learning Check Draw the condensed structural formula of the acetal formed by adding CH 3 OH to butanal.

28. Solution Draw the condensed structural formula of the acetal formed by adding CH 3 OH to butanal.

29. © 2013 Pearson Education, Inc. Chapter 14, Section 1 29 Learning Check Identify each as a chiral or achiral compound. A.B.C.

30. © 2013 Pearson Education, Inc. Chapter 14, Section 1 30 Solution Identify each as a chiral or achiral compound. A.B.C. chiral antichiral

31. © 2013 Pearson Education, Inc. Chapter 14, Section 1 31 Learning Check Indicate whether each of the following pairs of Fischer projections can or cannot be superimposed.

32. © 2013 Pearson Education, Inc. Chapter 14, Section 1 32 Solution Indicate whether each of the following pairs of Fischer projections can or cannot be superimposed: cannot be superimposed can be superimposed

33. © 2013 Pearson Education, Inc. Chapter 14, Section 1 33 Learning Check Identify the following as a D or L isomer.

34. © 2013 Pearson Education, Inc. Chapter 14, Section 1 34 Solution Identify the following as a D or L isomer. The –OH group is on the right, it is a D isomer.