Concept explainers
a. Rank the following alcohols from strongest to weakest acid:
b. Explain the relative acidities.
(a)
Interpretation:
The given alcohols have to be ranked from strongest to weakest acid.
Concept introduction:
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.
If an acid lose one proton, then the formed species is a conjugated base. Weak base forms stronger conjugated acid.
Acidity of species depends on the electronegativity of atom attached to the acidic proton. Order of electronegativity of hybridization is
Answer to Problem 47P
The given alcohols are ranked from strongest to weakest acid as follows,
Explanation of Solution
In hydrocarbons, if hydrogen atoms are replaced by electronegative atoms, it causes inductive electron withdrawal. It stabilizes its conjugate base thus increases the strength of the acid. The conjugated base of a weak acid is very strong. As the electronegativity of substituent increases, the greater will be the inductive electron withdrawal of the substituent making it a strong acid.
Therefore, the acidity order is:
The compound with three chlorine atoms near to the
(b)
Interpretation:
The relative acidities of the given alcohol compounds have to be explained briefly.
Concept introduction:
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.
If an acid lose one proton, then the formed species is a conjugated base. Weak base forms stronger conjugated acid.
Acidity of species depends on the electronegativity of atom attached to the acidic proton. Order of electronegativity of hybridization is
Explanation of Solution
In hydrocarbons, if hydrogen atoms are replaced by electronegative atoms, it causes inductive electron withdrawal. It stabilizes its conjugate base thus increases the strength of the acid. The electron density near
Want to see more full solutions like this?
Chapter 2 Solutions
Organic Chemistry
- Which of the following is the strongest acid? O a. acetic acid O b. dichlorobenzoic acid O c. dihydroxybenzoic acid Od. dichloro acetic acid e. chlorobenzoic acidarrow_forwardAnswer the following questions about esmolol, a drug used to treat high blood pressure sold under the trade name Brevibloc.a.Label the most acidic hydrogen atom in esmolol. b.What products are formed when esmolol is treated with NaH? c.What products are formed when esmolol is treated with HCl? d. Label all sp2 hybridized C atoms. e.Label the only trigonal pyramidal atom. f.Label all C's that bear a δ+ charge.arrow_forwardAnswer the following questions about esmolol, a drug used to treat high blood pressure sold under the trade name Brevibloc.a.Label the most acidic hydrogen atom in esmolol. b.What products are formed when esmolol is treated with NaH? c. What products are formed when esmolol is treated with HCl? d.Label all sp2 hybridized C atoms. e. Label the only trigonal pyramidal atom. f. Label all C's that bear a δ+ charge.arrow_forward
- Of the following compounds, the strongest acid is: a.propene b.tip (propino) c.propane d.cyclopropanearrow_forwardRank the compounds in each group in order of increasing basicity.arrow_forwardPyridine is a stronger base than pyrrole because the A. lone pair in pyridine is localized. B. lone pair in pyrrole is part of the continuous pi molecular orbital. C. lone pair in pyridine is more available for protonation. D. both A and B E. all of A, B, and Carrow_forward
- the aryl compound with higher basicity from the following compounds : Select one: a. H2N O b. H2N H2N d. H2N NO2 OCH3 CN CIarrow_forwardGive correct detailed Solutionarrow_forwardAnswer the following questions about the four species A–D.a.Which two species represent a conjugate acid–base pair? b. Which two species represent resonance structures? c. Which two species represent constitutional isomers?arrow_forward
- ety and labl the Lewis acid (electrophile) nd the Lewis base (mcleophile) in the fllowing actions Draw a curved arre tosho the mavement of electrons in the reaction and drew the predact o each reaction 21. What is the relationship betwoen the following two oompounds? A. Constitutional isomers B. Geonetric isomers C. kdentical compounds D. Different compounds 22. What is the relationship between the following two compounds? A. Constitutional isomers B. Geometric isomers C. Identical compounds D. Different compounds 23. Which pair of the following compounds are constitutional isomers? IV A. I and II B. Il and III C.l and IV D. I and IVarrow_forward15.44 Rank the following compounds in order of increasing acidity. A B Carrow_forward12) Which compound is stronger base? a) b) D A d) all the samearrow_forward
- Organic Chemistry: A Guided InquiryChemistryISBN:9780618974122Author:Andrei StraumanisPublisher:Cengage LearningChemistry for Today: General, Organic, and Bioche...ChemistryISBN:9781305960060Author:Spencer L. Seager, Michael R. Slabaugh, Maren S. HansenPublisher:Cengage Learning