Interpretation:
It is to be identified that the compound in each of the given pair reacts at a faster rate in an
Concept introduction:
The nucleophilic substitution reaction of methyl and primary
The nucleophilic substitution reaction of secondary and tertiary alkyl halide proceeds through
The
The
The formation of carbocation is the rate determining step in
The nucleophileattacks on the electrophilic carbon from opposite side of leaving group (i.e. backside attack) in
The nucleophilecan attacks from either face of planar carbocation in
The order of rate of alkyl halide toward substitution by nucleophiles on the basis of better leaving group is
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- Describe the stereochemistry of the bromohydrin formed in each reaction (each reaction is stereospecific). (a) cis-3-Hexene + Br2/H2O (b) trans-3-Hexene + Br2/H2Oarrow_forwardSelect the necessary reagent(s) for the following transformation.The answer is NOT Cu^2+ a. H+/H2O b. K2Cr2O7 c. NaOH d. H2/Pt e. Cu^2+ f. I2arrow_forwardHow does each of the following changes affect the rate of an E1 reaction?a.)Doubling [RX]b.)Doubling [B:]c.)Changing the halide from (CH3)3CBr to CH3CH2CH2Brarrow_forward
- Which set of reagents would be the bestchoice for the transformation shown below?A. 1. HgBr2/H2O 2. NaBH4B. Br2/H2OC. 1. Br2 2. H2OD. 1. Br2 2. NaOHE. 1. BH3 2. Br2 3. NaOH, H2O2, H2Oarrow_forwardWhich of the reagents would accomplish the transformation of 2-methyl-3-cyclopentanol into 2-methyl-3-cyclopentenone? A.) Br2, CCl4 B.) KMnO4 C.) H2, Pt D.) CrO3/H2SO4arrow_forwardPredict the major products of the following reactions, including stereochemistry where appropriate.(a) (R)@butan@2@ol + TsCl in pyridine (b) (S)-2-butyl tosylate + NaBr(c) cyclooctanol + NaOCl>HOAc (d) cyclopentylmethanol + CrO3 # pyridine # HCl(e) cyclopentylmethanol + Na2Cr2O7>H2SO4 (f) cyclopentanol + HCl>ZnCl2(g) n@butanol + HBr (h) cyclooctylmethanol + CH3CH2MgBr(i) potassium tert@butoxide + methyl iodide (j) sodium methoxide + tert@butyl iodide(k) cyclopentanol + H2SO4>heat (l) product from (k) + OsO4>H2O2, then HIO4(m) sodium ethoxide + 1@bromobutane (n) sodium ethoxide + 2@methyl@2@bromobutane(o) octan-1-ol + DMSO + oxalyl chloride (p) 4-cyclopentylhexan-1-ol + DMP reagentarrow_forward
- The expected major product from the treatment of 1-pentyne with 1 equivalent of HBr is: 1,2-dibromopentane 1-bromo-1-pentene 2-bromo-1-pentene 1,1-dibromopentane 2,2-dibromopentanearrow_forwardIdentify the product that can be obtained theoretically if the following reagents are mixed together: CH3CH2CH2CH2CH(OH)CH3 + PI3 5-Iodohexane Iodopentane 2-Iodohexane Iodohexanearrow_forwardPredict the product(s) you would expect from treatment of each compound with (1) dilute,neutral KMnO4 and (2) warm basic KMnO4, then dilute acid.(a) hex-1-yne (b) hex-2-yne (c) hex-3-yne(d) 2-methylhex-3-yne (e) cyclodecynearrow_forward
- Which of the following starting materials and reagents would be best to produce a racemic mixture of 3-methyl-3-hexanol? a. heptanone and 1. CH3MgBr 2. H3O+ b. hexanal and 1. CH3MgBr, 2. H3O+ c. 3-hexanone and 1. CH3MgBr, 2. H3O+ d. butanal and 1. CH3CH2MgBr, 2. H3O+arrow_forwardConsider the following E2 reaction.a.Draw the by-products of the reaction and use curved arrows to show the movement of electrons. b.What happens to the reaction rate with each of the following changes? [1] The solvent is changed to DMF. [2] The concentration of −OC(CH3)3 is decreased. [3] The base is changed to −OH. [4] The halide is changed to CH3CH2CH2CH2CH(Br)CH3. [5] The leaving group is changed to I−.arrow_forwardSelect the necessary reagent(s) for the following transformation. a. I2 b. H2/Pt c. Cu^2+ d. H+/H2O e. NaOH f. K2Cr2O7arrow_forward
- Organic ChemistryChemistryISBN:9781305580350Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. FootePublisher:Cengage Learning