Interpretation: The explanation for no formation of indicated alcohols from
Concept introduction: Hydroboration-oxidation involves a sequence of two reactions. The hydroboration stage involves the treatment of alkene with diborane that generates alkyl borane. In second stage, hydrogen peroxide in alkaline medium is used to oxidize the alkyl borane produced in step 1 that leads to the synthesis of alcohols from
Anti-Markovnikov’s Rule serves as the basis of hydroboration. It states that the negative part of reagent must go to the carbon that has less alkyl substituents or more
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EBK EXPERIMENTAL ORGANIC CHEMISTRY: A M
- (a) The Friedel-Crafts reaction of benzene with 2-chloro-3-methylbutane in the presence of AlCl3 occurs with a carbocation rearrangement. Give mechanistic explanation and the product formed. (b) Predict the product(s) will be formed from the following reactions: (i) Bromination of p-methylbenzoic acid (ii) Sulphonation of m-bromoanisole (iii) Friedel-craft acylation of o-bromonitrobenzenearrow_forwardAccount for the following relative rates of solvolysis under experimental conditions favoring S,1 reaction. CI CI Relative rate of 0.2 1 109 solvolysis (SN1)arrow_forwardFollowing compounds are given to you:2-Bromopentane, 2-Bromo-2-methylbutane, 1-Bromopentane(i) Write the compound which is most reactive towards SN2 reaction.(ii) Write the compound which is optically active.(iii) Write the compound which is most reactive towards β – elimination reactionarrow_forward
- Treatment of 1,3,6-cyclononatriene (Compound 1), or its dimethyl derivative (Compound 2), with potassium amide (KNH₂) in liquid ammonia results in the formation of anion 1a or 2a, respectively (J. Am. Chem. Soc. 1973, 95, 3437-3438): 9 15.85a 2 6 3 4 5 Compound 1 (R=H) Compound 2 (R=CH3) * You answer is incorrect. KNH₂ KNH₂ 1a (anion) 2a (anion) Of the following, which is NOT one of the four resonance structures of 1a?arrow_forwardGive the process of Determining the Mechanism and Stereochemistry inNucleophilic Substitution ?arrow_forwardDraw the structure of the products that will be formed when aniline reacts with nitrous acid at 5 oC,followed by:arrow_forward
- When bromomethane undergoes solvolysis in a solvent mixture composed of 90% water/10% acetone, the reaction rate is faster than when the same compound is solvolyzed in 80% water/20% acetone. Explain.arrow_forwardb) Compound A, C;H14 undergo hydration to form B which is optically active. Compound A reacts with cold alkaline potassium manganate (VII) to form C. Ozonolysis of compound A forms methanal and 3,3-dimethylbutanal. Deduce structure A, B, and C.arrow_forwardFor the reaction shown below (a) provide the structure of the major product (b) and a reasonable mechanism for its formation. CH3 Hg(OAc)2, H2SO4 (aq), H3Carrow_forward
- A task is assigned to an undergraduate student to test two samples (known as compounds K and L) in the laboratory. She placed these two compounds through various scientific tests. She discovered that these compounds have the same molecular formula, CSHSO. When treated with 2,4-dinitrophenylhydrazine, all of these compounds produce brightly coloured precipitate, and both are reduced to an organic compound with the molecular formula C§H100. However, compound K can be easily oxidized by chromic acid to formed compound N and vice versa for compound L. Furthermore, when both compounds react with Fehling's solutions, they produce negative results. However, only compound K forms a silver mirror when it reacts with Tollen's reagent, and compound L does not. Identify the possible structural formulae for compounds K, L, and N by ignoring their position isomerism. Indicate the formation of compound N from compound K. Predict the chemical reaction that occurs when compound L reacts with 2,4-…arrow_forward(b) Provide the reagents required and the intermediate products involved in the following multi-step syntheses. Br LL F 3 steps HO3S. Br SPh 3 steps Br NO2arrow_forwardProvide all resonance structures of the sigma complex when aniline reacts with an electrophile to yield the para-substituted product. Use -Br as an electrophile.arrow_forward
- Organic ChemistryChemistryISBN:9781305580350Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. FootePublisher:Cengage Learning