Download Ch 16-19 Review - Phillips Scientific Methods

Chapter 16-19 Review
Name ______________________________ #____
1. Draw the following aldehydes and ketones
a) hexanal
b) heptan-3-one
c) 3-methyloctanal
d) 2,2-dimethylhexan-3-one
e) 2,4,6-trichloroheptanal
f) 4-phenyloctan-2-one
g) 2-methylcyclohexanone
h) 4-hydroxyhexanal
i) penta-1,4-dione
2. Name the following aldehydes and ketones
H3C
H3C
CH2
O
CH3
CH
C
CH2
CH2
a)
b) H3C
O
CH2
CH2
H3C
CH
CH2
O
C
HC
CH3
CH2 HC
CH3
c)
CH3
CH3
H2C
C
O
H3C
CH3
CH
H2C
d)
CH2
H3C
CH
O
CH3
Cl
CH HC
C
O
e) O
CH
CH
CH3
f)
g)
CH3
CH2
C
CH
CH3
Br
3. Explain why no numeral is needed as a prefix in the naming of butanal and butanone.
4. Arrange the following compounds in increasing order of predicted solubility, and give reasons for your answers:
butanal, butane, butanol.
5. Rank #4 in terms of boiling point.
6. What is the product of the reduction of pentanal? Draw and name.
7. What is the product of the oxidation of 3-methyloctanal? Draw and name.
8. What is the product of oxidizing 3-pentanone?
8. How is a hemiacetal formed (no mechanism!)? Include functional groups of both reactants and product.
9. Draw 3-methyl-2-pentanone. Is it chiral or achiral? Explain.
10. Draw an enantiomer of 2-methylcyclopentanone. Is it R or S?
11. Draw the following carboxylic acids
a) butanoic acid
b) 2-methylpentanoic acid
c) 3,5-dimethylheptanoic acid
d) 5-hydroxyhexanoic acid
e) 2,3,4-trichlorobutanoic acid
f) 2-bromoethanoic acid
12. Name the following carboxylic acids
H3C
OH
CH2
a) H3C
CH2
CH2
H3C
C
CH2
CH2
CH3
O
C
C
CH3
b)
OH
O
CH
OH
CH2
c) HO
C
CH2
CH2
HO
CH3
C
CH2
O
F
H3C
H3C
HC
O
CH
CH2
C
C
F
d)
O
OH
e)
O
CH2
C
H3C
CH3
C
CH2
CH3
OH
f)
13. The labels have fallen off three bottles. Bottle A contains a gas, bottle B contains a liquid, and bottle C contains
a solid. The labels indicate that the compounds have the same number of carbon atoms, one being an alkane, one
an alcohol, and the other a carboxylic acid. Suggest the identity of the contents of each bottle, and give reasons for
your explanation.
14. Draw the following esters
a) ethyl butanoate
b) pentyl propanoate
c) propyl 3-ethylhexanoate
d) methyl 4-phenylpentanoate
e) 2,3-dimethylpentyl ethanoate
f) butyl 3-hydroxyheptanoate
15. Name the following esters
O
CH2
H3C
a)
O
C
CH2
CH2
O
CH3
H3C
b)
CH2
CH2
O
CH2
H3C
O
CH3
CH2
CH
C
c)
OH
C
O
CH3
O
H3C
O
O
CH3 CH3
C
O
C
C
CH3
CH3 CH3
d)
O
C
CH2
e) H3C
CH2
CH2
C
H3C
CH2
CH2
O
C
CH2
CH3
CH2
CH2
CH3
CH3
CH3 f)
16. In what way is the functional group of an ester different from that of a carboxylic acid? How does this difference
account for any differences in properties?
17. Describe the steps used to name an ester.
18. Draw the following amines
a) 1-butanamine
b) 2-pentanamine
c) 1,2-propandiamine
d) N-ethyl-hexan-2-amine
e) N,N-dimethyl-pentan-3-amine
19. Name the following amines
H3C
CH3
CH3
CH
CH
H3C
CH
H2C
CH3
CH2
CH3
d) H2N
CH2
CH2
CH2
CH HC
c)
H2N
NH2
CH3
CH2
N
e)
CH2
CH
NH2
CH2
Cl
CH2
NH2
b)
H3C
CH
Cl
CH
NH2
a)
CH3
H2C
CH2
H3C
CH3
f) H3C
NH
CH2
CH3
CH2
20. Explain why amines generally have lower boiling points than alcohols of comparable molar mass.
21. A-How are amines classified? B-Draw an example of each. C-Why are secondary and tertiary amines less
soluble than primary amines of similar molecular size?
22. In some cuisines, fish recipes include lemon garnish or a vinegar sauce such as sweet and sour sauce. Suggest
a reason why these common culinary techniques might be used.
23. Are amines acids or bases? Explain why.
24. Explain the general process of saponification (be able to recognize). See PPt and p. 482
25. Lab question: Explain the process you used in lab for synthesizing aspirin.
26. Lab question: Explain the process of esterification.
27. A- What process occurs for the synthesis of a triglyceride? B- Draw the reaction. C- What characterizes a
saturated FA from unsaturated and how does that affect properties between the two?
28. Which functional groups are in amino acids?
29. Give IUPAC for: formaldehyde, acetone, acetic acid, acetaldehyde, acetate
30. Know: aniline; derivatives of aniline using O,M,P; benzyl; ID purine vs pyrimidine (what biomolecules are they
part of?); ID a heterocyclic amine; naming unsymmetrical amines as N amines;
31. Go over properties of amines, aldehydes, ketones, acids, esters (see PPt). Ex-solubility, BP, polarity, odors, etc
32. Amine reactions to know: Ammonia with water (PPt); Rxn with acid (see PPt and p. 449/450- Do Prob 16.5)
33. What is a micelle? How does it work in detergents? See PPt and p. 483
34. What is a dimer?
35. What does reduction of pyruvate in cellular respiration yield?
36. Which of the following noncyclic (aliphatic) classes do not need #s in the IUPAC name for the location of the
functional group? Alcohol, Aldehyde, Ketone, Carboxylic Acid
37. What does hydrolysis of an ester yield? How does this relate to Fischer Esterfication?