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Interpretation:
The reactivity of the compounds,
Concept introduction:
Nucleophilic substitution reaction is a reaction where an electron rich species attacks a substrate which is electron deficient. When the solvent of the solution behaves as a nucleophile then it is known as solvolysis. Nucleophilic substitution reactions are of two types,
The unimolecular nucleophilic substitution reaction is
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Chapter 17 Solutions
Organic Chemistry
- Propose a synthesis of each of the following compounds, from the given starting material and any other needed reagents. 4. (a) -NO2 from (b) O,N- from -CH2-CH3arrow_forward4-Methyl-2-pentyne gives which product upon bromination followed by KOH/ethanol? (1) COOH (3) (4) Br Compound (1) a. Compound (2) Compound (3) OG. Compound (4) d.arrow_forwardExplain why 1-bromo-2,2-dimethylpropane has difficulty undergoing both SN2 and SN1 reactions. . Can it undergo E2 and E1 reactions?arrow_forward
- 4) Which reactant in each of the following pairs is more nucleophilic? Explain. BF3 and F H,0 and CH,CO2 (CH3)3P and (CH3)3N "CN and OCH3 (i) (ii) (iii) (iv)arrow_forwardWhat compound is the major product of the reaction sequence shown below? (1) KCN ethanol Он (A) NH2 (B) (2) LIAIH, (xS)/ether (3) dil. H* H;O он NH2 OH (C) (D) Compound C Compound D )Compound A O Compound Barrow_forwardA student wants to choose the best solvent for organometallic compounds such as Grignard reagents. Based on the three solvents below, explain which is the best solvent for Grignard reagents. (You must also explain why the others are not suitable). (c) `O-H ether ethanol ethyl acetatearrow_forward
- Which of the following reaction sequences would be best for converting compound I to compound II? OCH3 Br Compound I Το OCH3 Compound IIarrow_forwardIf anhydrides react like acid chlorides with the nucleophiles, draw the products formed when each of the following nucleophiles reacts with benzoic anhydride [(C6H5CO)2O]: (a) CH3MgBr (2 equiv), then H2O; (b) LiAlH4, then H2O; (c) LiAlH[OC(CH3)3]3, then H2O.arrow_forwardArrange these compounds in increasing order of reactivity in SN2 nucleophilic substitution?arrow_forward
- ) Draw all the Kekulé structures of anthracene and phenanthrene.(b) Propose mechanisms for the two additions shown.(c) In Chapter 8, most of the additions of bromine to double bonds gave entirely antistereochemistry. Explain why the addition to phenanthrene gives a mixture of synand anti stereochemistry.(d) When the product from (c) is heated, HBr is evolved and 9-bromophenanthrene results.Propose a mechanism for this dehydrohalogenationarrow_forwardArrange the compounds in order of INCREASING reactivity towards bromination. (from LEAST TO GREATEST) 1. Toluene, Nitrobenzene, Anisole, Aniline 2. Acetanilide, Benzaldehyde, Toluene, Iodobenzene 3. Acetophenone, Bromobenzene, Aniline, Phenolarrow_forwardFor each of the following pairs of species, which is the stronger nucleophile in acetone? Explain. (a) Hас — ОН or H,С (c) H3C-OH or H3C-NH, (b) or H,C-ÕH, (d) (e) (f) or or or `NH (g) (h) (i) CH;S CH3SE or or or `NH `PH (j) CH3SEarrow_forward
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