Chapter 12 Extra Credit

By Ziyun Chen
12.16 Identify the reagents you would use to achieve each of the following transformations:
12.17 Identify reagents that you could use to accomplish each of the following
transformations:
12.1 Provide an IUPAC name for each of the following alcohols:
 12.2 Safer alternatives to existing insecticides and mosquito repellants might be found in
the essential oils of plants. Phytol is one such isolated compound that has promising pest-
fighting potential.1 Provide the IUPAC name for phytol, which is both an alcohol and an
alkene. A 16-carbon alkane is called hexadecane (6 + 10 = 16), and you might find it helpful
to consult the textbook’s Appendix “Nomenclature of Polyfunctional Compounds” for
more help!
12.4 Draw the alkoxide ion that is formed in each of the following cases:
12.5 For each of the following pairs of alcohols, identify the one that is more acidic and
explain your choice:
 12.6 Flavonoids are a class of naturally occurring compounds with promising medicinal
uses due to their anti-inflammatory, anti-cancer and anti-HIV properties. Much of this
biological activ ity is due to the radical scavenging ability of flavonoids, which can be
affected by the acidity of their hydroxyl groups.2 Naringenin, the major flavonoid found in
grapefruit, has three acidic hydroxyl groups. pKa values are shown for two of these
hydroxyl groups (highlighted). Provide an explanation for the substantial difference in
acidity between these two hydroxyl groups.
 12.7 Identify the reagents that you would use to accomplish each of the following
transformations:
12.8 Identify reagents that can be used to achieve each of the following transformations: (a)
To convert 1-hexene into a primary alcohol (b) To convert 3,3-dimethyl-1-hexene into a
secondary alcohol (c) To convert 2-methyl-1-hexene into a tertiary alcohol
12.9 In each of the following transformations, identify whether the starting material has
been oxidized, reduced, or neither. Try to determine the answer without calculating -
oxidation states and then use the calculations to see if your intuition was correct.
 12.10 Compound 1 was converted into compound 2 and both compounds were evalu ated
for their cytotoxicity (ability to kill cells). It was observed3 that compound 2 was four to ten
times less cytotoxic than compound 1. Determine whether the ring has been oxidized,
reduced, or neither in this reaction. Try to determine the answer first by intuition and then
use calculations to see if your intuition was correct.
12.11 Draw a mechanism and predict the major product for each reaction:
12.12 Ambuic acid has been isolated from fungi that are frequently found associated with
economically important rain forest plant species. Ambuic acid is active against several
other fungi that are harmful to these plants, indicating that it may provide chemical
protection. During a synthesis of ambuic acid, compound 1 was reduced to compound 2
using NaBH4
12.13 Show how you would use a Grignard reaction to prepare each compound below:
 12.15 Extracts from the flowering plants of Asteraceae have been used to produce
medi cine, rubber, and pesticides. (+)-Carissone, a compound isolated from such extracts,
has been found to have antibacterial properties. During a synthesis of (+)-carissone, a
Grignard reaction was used to convert compound 1 into compound 2, as shown below
12.43 Draw a mechanism for each of the following reactions: