Concept explainers
(a)
Interpretation:
Reason for why
Concept Introduction:
According to the explanations by Bronsted-Lowry, if a species loses a proton then it is an acid whereas if a species receives one proton, then it is base.
If a base receives one proton, then the formed species is a conjugate acid whereas an acid lose one proton, then the formed species is a conjugated base.
Stronger the acid weaker it’s conjugate base and vice versa.
Deactivators are electron withdrawing groups attached to the benzenes that have either positive charge or an atom with high electronegativity. They are meta directors.
Activators are electron donating groups attached to the benzenes that have either electron density that is able to push into benzene ring or a lone pair of electrons. They are ortho–para directing.
(b)
Interpretation:
Reason for why the
Concept introduction:
According to the explanations by Bronsted-Lowry, if a species loses a proton then it is an acid whereas if a species receives one proton, then it is base.
If a base receives one proton, then the formed species is a conjugate acid whereas an acid lose one proton, then the formed species is a conjugated base.
Inductive effect: It is an electronic effect occurs due to the difference in the electronegativity of atoms in a bond. This unequal sharing of electrons in the bond leads to a permanent dipole.
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Chapter 23 Solutions
Organic Chemistry
- Write the chemical equation for the acid dissociation of acetaminophen, C8H9O2N. Write the Ka expression for the acid dissociation of acetaminophen.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(a) Given that Kb for ammonia is 1.8 x10-5 and that forhydroxylamine is 1.1 x 10-8, which is the stronger base?(b) Which is the stronger acid, the ammonium ion or thehydroxylammonium ion? (c) Calculate Ka values for NH4+and H3NOH+.arrow_forward
- Given that C6H11COOH has a pKa = 4.8 and C6H11N+H3 has a pKa = 10.7, (a) What pH would you make the water layer to cause the carboxylic acid to dissolve in the water layer and the amine to dissolve in the ether layer? (b) What pH would you make the water layer to cause the carboxylic acid to dissolve in the ether layer and the amine to dissolve in the water layer?arrow_forwardCompounds like amphetamine that contain nitrogen atoms are protonated by the HCl in the gastric juices of the stomach, and the resulting salt is then deprotonated in the basic environment of the intestines to regenerate the neutral form. Write proton transfer reactions for both of these processes.arrow_forward(a) Explain how NaBH, in CH;OH can reduce hemiacetal A to 1,4-butanediol (HOCH,CH,CH,CH,OH). (b) What product is formed when A is treated with Ph;P=CHCH,CH(CH),? (c) The drug isotretinoin is formed by reaction of X and Y. What is the structure of isotretinoin? Although isotretinoin (trade name Accutane or Roaccutane) is used for the treatment of severe acne, it is dispensed under strict controls because it also causes birth defects. PPha NaOCH,CH3 HO- isotretinoin HO A Br X Yarrow_forward
- The pkb of methylamine, CH3NH2, is 3.36. Calculate the pka of its conjugate acid, CH3NH3*. pka =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_forwardComplete the equation to show how pyridine, C, H, N, acts as a Brønsted-Lowry base in water. equation: C₂H₂N+H₂O=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_forwardExplain why CH3 CH2 CH2NH2 is a Brønsted base. Its water solutions are basic. All substances containing nitrogen atoms are Brønsted bases. This amine is a proton donor. This amine can ассеpt a proton from a proton donor.arrow_forwardBecause amines are basic, they can often accept a proton. Draw the protonated structure of n-propylamine.arrow_forward
- Organic ChemistryChemistryISBN:9781305580350Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. FootePublisher:Cengage Learning