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Oh ho oh ho oh o o o o ho o o ho o oxalic acid pk a1

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OH HO OH HO OH O O O O HO O O HO O oxalic acid pK a1 = 1.3 pK a2 = 4.2 malonic acid pK a1 = 2.8 pK a2 = 5.7 succinic acid pK a1 = 4.2 pK a2 = 5.6 O OH adipic acid pK a1 = 4.3 pK a2 = 5.4 4. Rank the following sets of molecules in order of increasing to decreasing acidity ( 1 = strongest acid, 4 = weakest acid). Provide a brief explanation for your choices. H 3 C N CH 3 H CH 3 + Cl N CH 3 H CH 3 + A B C D O OH H 3 C H 3 C CH 3 OH O OH O O O OH O CH 3 Cl Cl CH 3 A B C D H 2 N NH 2 O H + H 2 N H O H + Chem 33, Kanan & Stack, 2012, PS 3; pg 2
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5. Usually the cis / trans nomenclature system is adequate to distinguish alkene isomers, but not always. The two isomers of 2-chlorobut-2-ene (C 4 H 7 Cl) have 3-non-hydrogen substituents attached to the double bond. In such cases, the Z/E nomenclature system is used. Z implies that highest ordered substituent on each carbon of the double bond are positioned on the same side of the double bond ( Z ame Z ide), while E implies that the highest ordered substituents on each carbon of the double bond are on opposite ( E pposite) sides. For this nomenclature to work, both substituents on each carbon center of the double bond need to be prioritized. The most important rule is that the higher atomic number atom directly attached to the carbon center of a double bond receives the higher priority ( e.g. , Cl > C > H). Remember that the prioritization occurs independently at each carbon atom of the alkene. If an ambiguity persists ( e.g. an methyl and ethyl chain bonded to a single carbon of the alkene), the higher priority is assigned to the substituent that has the highest atomic number in the second position of the substituent chain ( i.e. CH 3 CH 2 > CH 3 ). If the two highest priority substituents on each carbon of the alkene reside on the same side of the double bond, this isomer is designated Z, while opposite positioning results in an E designation.
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