Concept explainers
(a)
Interpretation:
The most acidic proton, in the given species, is to be identified, and its pKa value is to be estimated.
Concept introduction:
An Acidic proton is one which is directly bonded to an electronegative atom. The acidity of a compound is governed largely by the functional group on which the acidic proton is found. Nearby structural features such as highly electronegative substituent or presence of a double or triple bond can alter the acidity significantly. The pKa value for a particular compound is explained based on structural similarities of the compound and the compounds listed in Table 6-1.
Answer to Problem 6.50P
The most acidic proton in the given species along with its estimated pKa value is:
Explanation of Solution
The structure for the given compound is:
There are three protons that could be acidic. The proton attached to the carbon in methyl group, to the oxygen atom in alcohol, and the proton directly attached to the oxygen atom in phenol functional group are the protons that could be acidic.
According to Table 6-1, the relative pKa value of each of the protons is:
The pKa value for the compound having
The pKa value for the compound having
The pKa value for the compound having
Lower the pKa value, stronger is the acid, and the proton associated with it is the most acidic proton. The lowest pKa value is for
The most acidic proton in the given structure is identified along with its estimated pKa value using Table 6-1.
(b)
Interpretation:
The most acidic proton in the given species is to be identified and its pKa value is to be estimated.
Concept introduction:
An Acidic proton is the one which is directly bonded to an electronegative atom. The acidity of a compound is governed largely by the functional group on which the acidic proton is found. Nearby structural features such as highly electronegative substituent or presence of a double or triple bond can alter the acidity significantly. The pKa value for a particular compound is explained based on structural similarities of the compound and the compounds listed in Table 6-1.
Answer to Problem 6.50P
The most acidic proton in the given species along with its estimated pKa value is:
Explanation of Solution
The structure for the given compound is:
In the given structure, the proton attached to the nitrogen atom, and to the carbon atom next to the carbonyl group, could be the acidic protons.
According to Table 6-1, the relative pKa value of each of the protons is:
The pKa value for the compound having
The pKa value for the compound having
Lower the pKa value, stronger is the acid, and the proton associated with it is the most acidic proton. The lowest pKa value is for
The most acidic proton in the given structure is identified along with its estimated pKa value using Table 6-1.
(c)
Interpretation:
The most acidic proton in the given species is to be identified and its pKa value is to be estimated.
Concept introduction:
An Acidic proton is the one which is directly bonded to an electronegative atom. The acidity of a compound is governed largely by the functional group on which the acidic proton is found. Nearby structural features such as highly electronegative substituent or presence of a double or triple bond can alter the acidity significantly. The pKa value for a particular compound is explained based on structural similarities of the compound and the compounds listed in Table 6-1.
Answer to Problem 6.50P
The most acidic proton in the given species along with its estimated pKa value is:
Explanation of Solution
The structure for the given compound is:
There are two protons that could be acidic. The proton attached to the oxygen atom which is directly bonded to the carbonyl group, and to the sulfur atom are the protons that could be acidic.
According to Table 6-1, the relative pKa value of each of the protons is:
The pKa value for the compound having
The pKa value for the compound having
Lower the pKa value, stronger is the acid and the proton associated with it is the most acidic proton. The lowest pKa value is for
The most acidic proton in the given structure is identified along with its estimated pKa value using Table 6-1.
(d)
Interpretation:
The most acidic proton in the given species is to be identified and its pKa value is to be estimated.
Concept introduction:
An Acidic proton is the one which is directly bonded to an electronegative atom. The acidity of a compound is governed largely by the functional group on which the acidic proton is found. Nearby structural features such as highly electronegative substituent or presence of a double or triple bond can alter the acidity significantly. The pKa value for a particular compound is explained based on structural similarities of the compound and the compounds listed in Table 6-1.
Answer to Problem 6.50P
The most acidic proton in the given species along with its estimated pKa value is:
Explanation of Solution
The structure for the given compound is:
In the given structure, the proton attached to the nitrogen atom and to the triple bonded carbon atom could be the acidic protons.
According to Table 6-1, the relative pKa value of each of the protons is:
The pKa value for the compound having
The pKa value for the compound having
Lower the pKa value, stronger is the acid and the proton associated with it is the most acidic proton. The lowest pKa value is for
The most acidic proton in the given structure is identified along with its estimated pKa value using Table 6-1.
(e)
Interpretation:
The most acidic proton in the given species is to be identified and its pKa value is to be estimated.
Concept introduction:
An Acidic proton is the one which is directly bonded to an electronegative atom. The acidity of a compound is governed largely by the functional group on which the acidic proton is found. Nearby structural features such as highly electronegative substituent or presence of a double or triple bond can alter the acidity significantly. The pKa value for a particular compound is explained based on structural similarities of the compound and the compounds listed in Table 6-1.
Answer to Problem 6.50P
The most acidic proton in the given species along with its estimated pKa value is:
Explanation of Solution
The structure for the given compound is:
There are two protons that could be acidic. The proton attached to the carbon in methyl group, to the oxygen atom in alcohol, and the proton directly attached to the oxygen atom in phenol functional group are the protons that could be acidic.
According to Table 6-1, the relative pKa value of each of the protons is:
The pKa value for the compound having
The pKa value for the compound having
Lower the pKa value, stronger is the acid and the proton associated with it is the most acidic proton. The lowest pKa value is for
The most acidic proton in the given structure is identified along with its estimated pKa value using Table 6-1.
(f)
Interpretation:
The most acidic proton in the given species is to be identified and its pKa value is to be estimated.
Concept introduction:
An Acidic proton is the one which is directly bonded to an electronegative atom. The acidity of a compound is governed largely by the functional group on which the acidic proton is found. Nearby structural features such as highly electronegative substituent or presence of a double or triple bond can alter the acidity significantly. The pKa value for a particular compound is explained based on structural similarities of the compound and the compounds listed in Table 6-1.
Answer to Problem 6.50P
The most acidic proton in the given species along with its estimated pKa value is:
Explanation of Solution
The structure for the given compound is:
There are two protons that could be acidic. The proton attached to the carbon in methyl group, to the oxygen atom in alcohol, and the proton directly attached to the oxygen atom in phenol functional group are the protons that could be acidic.
According to Table 6-1, the relative pKa value of each of the protons is:
The pKa value for the compound having protonated
The pKa value for the compound having
Lower the pKa value, stronger is the acid and the proton associated is the most acidic proton. The lowest pKa value is for protonated
The most acidic proton in the given structure is identified along with its estimated pKa value using Table 6-1.
(g)
Interpretation:
The most acidic proton in the given species is to be identified and its pKa value is to be estimated.
Concept introduction:
An Acidic proton is the one which is directly bonded to an electronegative atom. The acidity of a compound is governed largely by the functional group on which the acidic proton is found. Nearby structural features such as highly electronegative substituent or presence of a double or triple bond can alter the acidity significantly. The pKa value for a particular compound is explained based on structural similarities of the compound and the compounds listed in Table 6-1.
Answer to Problem 6.50P
The most acidic proton in the given species along with its estimated pKa value is:
Explanation of Solution
The structure for the given compound is:
In the given structure, the proton attached to both nitrogen atoms could be acidic protons.
According to Table 6-1, the relative pKa value of each of the protons is:
The pKa value for the compound having protonated
The pKa value for the compound having
Lower the pKa value, stronger is the acid and the proton associated with it is the most acidic proton. The lowest pKa value is for protonated
The most acidic proton in the given structure is identified along with its estimated pKa value using Table 6-1.
(h)
Interpretation:
The most acidic proton in the given species is to be identified and its pKa value is to be estimated.
Concept introduction:
An Acidic proton is the one which is directly bonded to an electronegative atom. The acidity of a compound is governed largely by the functional group on which the acidic proton is found. Nearby structural features such as highly electronegative substituent or presence of a double or triple bond can alter the acidity significantly. The pKa value for a particular compound is explained based on structural similarities of the compound and the compounds listed in Table 6-1.
Answer to Problem 6.50P
The most acidic proton in the given species along with its estimated pKa value is:
Explanation of Solution
The structure for the given compound is:
In the given structure, the protons attached to the terminal triple bonded carbon atom and to the nitrogen atom could be acidic protons.
According to Table 6-1, the relative pKa value of each of the protons is:
The pKa value for the compound having protonated
The pKa value for the compound having
Lower the pKa value, stronger is the acid and the proton associated with it is the most acidic proton. The lowest pKa value is for
The most acidic proton in the given structure is identified along with its estimated pKa value using Table 6-1.
Want to see more full solutions like this?
Chapter 6 Solutions
ORGANIC CHEMISTRY PRINCIPLES & MECHANISM
- (i) Identify the acidic proton(s) for each of the following carbonyl compounds: O O ( CHỊCH, CÁCH, BỊ CHỊCHỊCH, CÁCH, (2) || (3) CHy-O-C-CH,-C-O-CH, (4) CH,-C-CH, (ii) Rank the compounds (in part (i) above) in the order of increasing or decreasing acidity by using the symbol "" in your answer.arrow_forwardAs we will see in later chapters, many steps in key reaction sequences involve acid–base reactions. (a) Draw curved arrows to illustrate the flow of electrons in steps [1]–[3]. (b) Identify the base and its conjugate acid in step [1]. (c) Identify the acid and its conjugate base in step [3].arrow_forwardRank the following conjugate bases in order of decreasing basicity, putting the most basic first. H2C=CH HC=C CH3 II Multiple Choice || > |> |II |> || > III III > || > | III > | > ||arrow_forward
- Using 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_forwarda.) Rank the attached compounds in order of increasing acidity. (b)Which compound forms the strongest conjugate base?arrow_forwardWhich of the following anions is the stronger base? Explain your choice.arrow_forward
- What is the increasing order of basicity among the following compounds ? I NH OH | < | < III < IV OIV < III < II < 1 I < III < II < IV OII < | < ||| < |V || < ||| < | < IV II NH III NH OH IV OH NHarrow_forwardRank the following structures in order of increasing basicity. NH₂ NH₂ vergren NH₂ A) | < || < ||| B) || < ||| < | C) III < | < || D) | < ||| < || E) III < ||arrow_forward(a) Rank the following compounds in order of increasing acidity. (b) Which compound forms the strongest conjugate base?arrow_forwardWhich is a stronger acid and has the most stable conjugate base? Estimate the pKA values for both compounds.arrow_forwardно HO но он The pK, of ascorbic acid (vitamin C) is 4.17, showing that it is slightly more acidic than acetic acid (CH3CO0H, pKa 4.74). (a) Show the fou r different conjugate bases that would be formed by deprotonation of the four different OH groups in ascorbic acid. (b) Compare the stabilities of these four conjugate bases, and predict which OH group of ascorbic acid is the most acidic. (c) 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_forwardAs we will see in later chapters, many steps in key reaction sequencesinvolve acid–base reactions. (a) Draw curved arrows to illustrate the flow of electrons in steps [1]–[3]. (b) Identify the base and its conjugate acid in step [1]. (c) Identify the acid and its conjugate base in step [3].arrow_forwardarrow_back_iosSEE MORE QUESTIONSarrow_forward_ios
- Organic Chemistry: A Guided InquiryChemistryISBN:9780618974122Author:Andrei StraumanisPublisher:Cengage LearningOrganic ChemistryChemistryISBN:9781305580350Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. FootePublisher:Cengage Learning