Interpretation: The possible structures of the conjugate acids of acetic acid are to be drawn. An explanation corresponding to the fact that in acetic acid the correct conjugate acid more stable is to be explained. The
Concept introduction: According to Bronsted-Lowry theory, when an acid donates a proton the species formed is known as conjugate base and when the base accepts a proton the species formed is known as conjugate acid. The conjugate base has negative charge or lone pair of electrons present over it.
The acidity and basicity of a compound is influenced by the resonance. The amount of stability depends on the delocalization of the charge through the resonance. The delocalization of electrons due to presence of lone pair and double bond is called resonating structure.
To determine: The possible structures of the conjugate acids of acetic acid,
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Chapter 2 Solutions
EP ORGANIC CHEMISTRY -MOD.MASTERING 18W
- 4. The pk, of vanillin is about 9, which is much more acidic than a normal alcohol. Draw a reaction showing the deprotonation of vanillin with NaOH, and then draw six resonance structures of the conjugate base. Draw the hybrid structure and clearly indicate how the negative charge is distributed in the compound.arrow_forwardexplain in great detail why the pKa values are what they are and compare them among the three compounds. The conjugate acids that are protonated are drawn in red for each compound. Which one based on the pKa is most acidic and what does that tell you about how basic their lone pairs are?arrow_forwardUsing pKa Values to Determine Relative Acidity and Basicity Rank the following compounds in order of increasing acidity, and then rank their conjugate bases in order of increasing basicity.arrow_forward
- The pKa of ascorbic acid (vitamin C, page 55) is 4.17, showing that it is slightly more acidic than acetic acid (CH3COOH, pKa 4.74). Compare the most stable conjugate base of ascorbic acid with the conjugate base of acetic acid, and suggest why these two compounds have similar acidities, even though ascorbic acid lacks the carboxylic acid (COOH) group.arrow_forward(i) Draw the dissociation reaction for a carboxylic acid in water and define the Ka for this reaction. Write the equation that relates pKa to Ka. (ii) A deprotonated carboxylic acid can be drawn in two resonance forms. Draw the two forms and explain what the term “resonance” means. (iii) Draw an energy profile for the above dissociation reaction and describe how the profiles for a strong and a weak acid would differ.arrow_forwardFrom each pair, select the stronger base. Then draw the conjugate acid of the stronger base below. CICH,CH,0¯ or CH;CH,0- • You do not have to consider stereochemistry. • You do not have to explicitly draw H atoms. • You do not have to include lone pairs in your answer. opy aste [Farrow_forward
- Squaric acid has a pKa of 1.5, making it much more acidic than many carboxylic acids (typical pKa values of 4–5). One of the reasons for its acidity is resonance stabilization of its conjugate base, which is shown below. Add curved arrows to the structure on the left to show how it is converted to the other resonance contributor shown to the right.arrow_forwardWhich of the following has the lowest pka value? Hint: a methyl group is an electron donating group which can destabilize the negative charge of the conjugate base. * I CH,COOH I HCOOH 1 (CH),CH – COOH II CH,CH,COH IVarrow_forwardIndicate which is the weaker base and explain why. Be specific! NH3 or NF3arrow_forward
- Sulfuric acid (H2SO4) has a pKa value of -10 and it is almost completely ionized in water. Write the ewis structure for the conjugate base of sulfuric acid. Draw all the possible resonance structures for the corresponding conjugate base.arrow_forwardGive typed explanation Which is the strongest base?arrow_forwardDefine why are protons on an alpha carbon of an aldehyde or ketone more acidic than a proton on an alpha carbon of an ester? What are their pKa's?arrow_forward
- Organic Chemistry: A Guided InquiryChemistryISBN:9780618974122Author:Andrei StraumanisPublisher:Cengage Learning
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