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The octanol-water partition

1) A paper published earlier this year by Berens et al., (2020, EST) examined the reduction of 2,4-dinitroanisole (DNAN) one of the new generation of insensitive munitions explosives that has become an environmental problem at many Department of Defense facilities. They report that DNAN forms two isomers, 6-methoxy, 3-nitroaniline (also known as 2-amino-4-nitroanisole) and 4-methoxy, 5-nitroaniline (also known as 4-amino-2-nitroanisole). Please answer the following questions.
• Calculate the octanol-water partition coefficient using the atom/fragment contribution method. Note that you need to only do this once because they are structural isomers. (10)
• There is no “experimental” pKa values for both isomers. Please estimate their pKa values using the Hammett-Taft model. (15)
• A different paper by Li et al., (2013, J. Haz. Materials) examined the oxidation of DNAN by ultrasound and the Fenton reaction. They ran their experiments at a pH of 2.7.
i. Determine the speciation of both compounds at this pH i.e., what fraction is protonated vs. neutral. (10)
ii. Recalculate the octanol-water partition coefficients for both isomers at this pH. What is the principal reason behind any difference in your calculated values given that the isomers have the same calculated Kow? (5)

2) A paper by Rudel et al. (EST 2003, 4543) measured the concentration of various pollutants in indoor air. They report respective average levels of 1560 and 426 ng/M3 for diethyl phthalate (DEP) and di-n-butyl phthalate (DBP), which are both present in most plastics (use Chemspider to get additional data).

• If these levels are present in your house and you have a bottle of extra virgin olive oil open to the air at 30o C (its summertime), how much of each compound will be in the oil phase (mol/L)? You can assume Raoult’s Law is obeyed and a respective molecular weight and density for the olive oil of 160 g/mol and 0.9 g/ml. (25)
• What is the air-olive oil partition coefficient for these two compounds at 25 C based upon:
o The assumption that Raoult’s Law is obeyed (15)
o Estimated based upon the pp-LFER provided in the book (Table 10.2) and the UFZ database. Is the assumption that Raoult’s Law is obeyed a reasonable one? If not what is the activity coefficient for each compound in olive oil? (20)

Sample Solution

Consequently, jus ad bellum comprises several conditions but most importantly: just cause and proportionality. This gives people a guide whether it’s lawful to enter a war or not. However, this is only one part of the theory of the just war. Nevertheless, it can be seen above that jus ad bellum can be debated throughout, showing that there is no definitive theory of a just war, as it is normatively theorised. The second section begins deciphering jus in bello or what actions can we classify as permissible in just wars (Begby et al (2006b), Page 323). First, it is never just to intentionally kill innocent people in wars, supported by Vittola’s first proposition. This is widely accepted as ‘all people have a right not to be killed’ and if a soldier does, they have violated that right and lost their right. This is further supported by “non-combatant immunity” (Frowe (2011), Page 151), which leads to the question of combatant qualification mentioned later in the essay. This is corroborated by the bombing of Nagasaki and Hiroshima, ending the Second World War, where millions were intently killed, just to secure the aim of war. However, sometimes civilians are accidentally killed through wars to achieve their goal of peace and security. This is supported by Vittola, who implies proportionality again to justify action: ‘care must be taken where evil doesn’t outweigh the possible benefits (Begby et al (2006b), Page 325).’ This is further supported by Frowe who explains it is lawful to unintentionally kill, whenever the combatant has full knowledge of his actions and seeks to complete his aim, but it would come at a cost. However, this does not hide the fact the unintended still killed innocent people, sho

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