Interpretation:
Given that phenylboronic acid upon nitration gives 15% orthosubstitution product and 85% meta product. The meta directing effect of the –B(OH)2 group is to be explained.
Concept introduction:
The substituents attached to the ring have a strong influence on the incoming electrophile. Electron releasing substituent groups, except halogens, activate the ring and direct the incoming electrophile to the o- and p- positions. Halogens are o- and p- directors but they deactivate the ring. Electron withdrawing substituent groups deactivate the ring and direct the incoming electrophile to the m- position. Boron compounds are usually electron acceptors as in these compounds boron is electron deficient.
To explain:
The meta directing effect of the –B(OH)2 group as upon nitrating phenylboronic acid 15% orthosubstitution product and 85% meta product are obtained.
Trending nowThis is a popular solution!
Chapter 16 Solutions
Bundle: Organic Chemistry, Loose-leaf Version, 9th + LMS Integrated for OWLv2, 4 terms (24 months) Printed Access Card
- (R)-Pulegone is converted to (R)-citronellic acid by addition of HCl followed by treatment with NaOH. Propose a mechanism for each step in this transformation and account for the regioselectivity of HCl addition.arrow_forwardThe pKa, of the conjugate acid of morpholine is 8.33. (a) Calculate the ratio of morpholine to morpholinium ion in aqueous solution at pH 7.0. (b) At what pH are the concentrations of morpholine and morpholinium ion equal?arrow_forwardWhat is the purpose of HCl in the iodination of vanillin. And what is the complete mechanism for this reaction, along with how do you synthesize the catalyst and electrophil I-Cl.arrow_forward
- The pKas of chemicals HX and HY are 5 and 7 respectively. The pKa of carbonic acid H2CO3is 6. If you made up an ether solution of chemicals HX and HY in a separatory funnel, andthen added an aqueous solution of sodium bicarbonate NaHCO3 to that separatory funnel,would both HX and HY stay in the ether layer? Or would either or both of them transfer intothe aqueous layer? If one goes into the water layer, will it be in it’s neutral HX/HY form, or init’s deprotonated anionic form?arrow_forwardWhen pyrrole is added to a dilute solution of D2SO4 in D2O, 2-deuteriopyrrole is formed. Propose a mecha-nism to account for the formation of this compound.arrow_forwardAnilinium ion, PhNH3+ , Catalyze semicarbazone formation from benzaldhyde much more effectively than would be expected on the basis of its strength as an acid. Explain.arrow_forward
- The deuterium kinetic isotope effect (kH2O/kD2O) for the hydrolysis of aspirin is 2.2. What does this tell you about the kind of catalysis exerted by the ortho-carboxyl substituent? (Hint: It is easier to break an O¬H bond than an O¬D bond.)arrow_forwardGive the expected products of lithium aluminum hydride reduction of the followingcompounds (followed by hydrolysis).(a) butyronitrile (b) N-cyclohexylacetamide (c) e@caprolactamarrow_forwardWhy cis-Ru(II)Cl2(DMSO)4 reacts with pyridine, et cetera, to give substitution of the DMSO but not the chloride ligands, but trans-Ru(II)Cl2(py)4 react with suitable Na+ and K+ salts in aqueous pyridine to afford chloride-substituted derivatives. write the reactions equations.arrow_forward
- Compare the 13C NMR spectra of isoborneol and camphor. Explain which peaks can be used to determine whether the oxidation was successful. Propose a mechanism for this oxidation. To simplify the structures, use benzyl alcohol to draw the mechanism instead of isoborneol. Include the formation of any byproduct(s) in the mechanism.arrow_forwardWhat is the reaction mechanism of ethyl acetate with alkaline I2 in KI? Indicate the compound responsible for the observed turbidity.arrow_forwardExplain the reactions involved in separation of p-nitroaniline from mixture contain 3 components 1.Benzoic acid (acidic nature pKa=4.17) 2.Naphthalene (neutral compound) 3.paraNitroaniline(basic compound pKa=12.99arrow_forward
- Organic ChemistryChemistryISBN:9781305580350Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. FootePublisher:Cengage Learning