Concept explainers
Interpretation:
The reaction between
Concept introduction:
Lewis acids are electron pair acceptors.
Lewis bases are electron pair donors.
Any electron deficient species can act as a Lewis acid such as compounds containing group IIIA elements like Boron or Aluminum.
Compounds having vacant orbitals also act as Lewis acids like halides of Iron, Zinc and Aluminum.
Electron loving or seeking compounds are called Electrophiles.
All Lewis acids are electrophiles but all electrophiles are not Lewis acids
Electron donating compounds are called Nucleophiles.
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Chapter 3 Solutions
Organic Chemistry, 12e Study Guide/Student Solutions Manual
- How do triphenylphosphine and borane form a Lewis acid-base adduct? (a) The phosphorus atom in triphenylphosphine is less electronegative than the boron atom in borane and is thus attracted to boron to form the bond. (b) The phosphorus in triphenylphosphine exchanges with the boron from borane. (c) Triphenylphosphine donates the lone pair on its phosphorus to the electron-deficient boron in borane. (d) Triphenylphosphine donates a phenyl ring from its phosphorus to the electron-deficient boron in borane. (e) The phosphorus in triphenylphosphine accepts a proton from the proton-rich borane.arrow_forwardEthanol, Phenol, picric acid Arrange them according to the increasing acidity. Explain why and include the drawing of their structure to support your answer.arrow_forwardGive reasons: (i) Bond length of C = O in carboxylic acids is slightly larger than C = O bond length in carbonyl compounds. (ii) There are two –NH2 groups in semicarbazide. However, only one –NH2 group is involved in the formation of semicarbazones. (iii) Benzoic acid is less soluble in water than acetic acid. (iv) Formic acid is a stronger acid than acetic acid.arrow_forward
- PRACTICE PROBLEM 2.25 The compounds in each part below have the same (or similar) molecular weights. Which compound in each part would you expect to have the higher boiling point? Éxplain your answers. OH or HO. (a) (c) но OH or (b) (CHa),N orarrow_forwardInterpret the acidity of alcohols on the basis of ground-state polarization and stability of the alcoholate anion(indicate and give symbols for bond polarization)! Compare the relative acidity of ethanol and 2-fluoroethanol!arrow_forwardquestion (a) and (b) onlyarrow_forward
- give the scheme of Acetic acid to Terephthalic acidarrow_forwardIdentify which of the following compounds is most acidic along with the best supporting explanation. O (1) is more acidic as the resulting conjugate base is an aromatic anion. O (11) is more acidic as the resulting conjugate base is an aromatic anion. O (1) is more acidic because the compound has two pi bonds. O (I1I) is more acidic due to the large angle strain in the cyclopropene. O () is more acidic due to less angle strain in the cyclopentadienearrow_forward4.3 Explain why each of the following groups is useful in organic synthesis. Use suitable examples and chemical equations to illustrate your answers. (i) (ii) (iii) Benzyl ester group Carboxybenzyl (Cbz) group t-Butyloxycarbonyl (Boc) grouparrow_forward
- Why does structure have 6 pi bonds? I understand Huckel's rule which determines if a structure is aromatic or not. Please explain which structures are aromatic according to the options givenarrow_forward(a) Although phenoxide ion has more number of resonating structures than carboxylate ion, carboxylic acid is a stronger acid than phenol. Give two reasons.(b) How will you bring about the following converstions?(i) Propanone to propane (ii) Benzoyl chloride to benzaldehyde(iii) Ethanal to but-2-enalarrow_forwardFor each of the following structures,1. Draw a Lewis structure; fill in any nonbonding electrons.2. Calculate the formal charge on each atom other than hydrogen.(a) CH3NO(nitromethane)(b) (CH3)3NO(trimethylamine oxide)(c) [N3]-(azide ion)(d) [(CH3)3O]+ (e) CH3NC (f) (CH3)4NBrarrow_forward
- Organic Chemistry: A Guided InquiryChemistryISBN:9780618974122Author:Andrei StraumanisPublisher:Cengage Learning