Interpretation:
The feature of the molecule that responsible for such lack of reactivity for
Concept Introduction:
The
The first step of
Frist step is the slow step also rate determining step so the rate of the reaction is depends on the concentration of substrate only.
Nucleophile attacks the both front and back side of carbocation in
Order of the substrate that favored in
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Chapter 9 Solutions
Organic Chemistry
- Alcohols are important for organic synthesis, especially in situations involving alkenes. The alcohol might be the desired product, or the OH group might be transformed into another functional group via halogenation, oxidation, or perhaps conversion to a sulfonic ester derivative. Formation of an alcohol from an alkene is particularly powerful because conditions can be chosen to produce either the Markovnikov or non-Markovnikov product from an unsymmetrical alkene. Using your reaction roadmap as a guide, show how to convert 4-methyl-1-pentene into 5-methylhexanenitrile. You must use 4-methyl-1-pentene and sodium cyanide as the source of all carbon atoms in the target molecule. Show all reagents needed and all molecules synthesized along the way.arrow_forward(c) Hydrolysis of the haloalkane shown below results in the formation of two alcohols B and C that are stereoisomers of each other. Give the structures of the alcohols B and C and propose a mechanism for their formation ensuring that you explain the stereochemical outcome observed. H3CH2C CH3 H20, heat Br H. B + Carrow_forward(c) Hydrolysis of the haloalkane shown below results in the formation of two alcohols B and C that are stereoisomers of each other. Give the structures of the alcohols B and C and propose a mechanism for their formation ensuring that you explain the stereochemical outcome observed. H3CH2C CH3 H20, heat Br B + Carrow_forward
- When the alkyl bromides (listed here) were subjected to hydrolysis in a mixture of ethanol and water (80% EtOH/20% H2O) at 55 °C, the rates of the reaction showed the following order: (CH3)3CBR > CH3Br > CH3CH2Br > (CH3)2CHBR Provide an explanation for this order of reactivity.arrow_forwardYou are required to synthesize 2-bromopentane from the reaction between an alkene with HBr. Which alkene, 1-pentene or 2-pentene, should you react with HBr in order to get 2-bromopentane? Give an explanation.arrow_forwardFour carbocations are shown, which can possibly rearrange via hydride shift to a more stable carbocation. Compound A consists of two fused cyclohexane rings where a carbocation is on one of the fused carbons. Compound B consists of a linear pentane chain with a carbocation on carbon 2. Compound C consists of a linear pentane chain where carbon 3 is bonded to a CH 2 plus. Compound D consists of a cyclohexene where the carbocation is on carbon 1 and an alkene on carbons 3 and 4. Select the carbocation(s) that will rearrange via hydride shift. OC O Aarrow_forward
- In SN2 reactions of haloalkanes, the order of reactivity is RI>RBr>RCl>RF. Alkyl iodides are considerably more reactive than alkyl fluorides, often by factors as great as 106. All 1-halo-2,4-dinitrobenzenes, however, react at approximately the same rate in nucleophilic aromatic substitutions. Account for this difference in relative reactivities.arrow_forwardThe reaction of 2,2-dimethyl-1-propanol [(CH3)3CCH2OH], also known by the common name neopentyl alcohol, with HBr is very slow and gives 2-bromo-2-methylbutane as the major product.Give a mechanistic explanation for these observations.arrow_forwardYou are planning to carry out a reaction between propyne, CH3C≡CH and sodium amide, NaNH2. You also need to choose an appropriate solvent for carrying out the reaction. Would ethanol be suitable for this purpose? Explain your rationale clearly.arrow_forward
- The reaction of 1-iodopropane with potassium thiocyanate (KSCN) in certain solvents results in the formation of two isomeric products, propylthiocyanate and propylisothiocyanate (see scheme below), via the SN2 reaction mechanism. Attempts to prepare a similar mixture of these same isomeric products (propylthiocyanate and propylisothiocyanate) starting from 1-propene is illustrated below. Despite the strong acidity of thiocyanic acid (recall pKa = 1.1), this addition reaction does not lead to either of the products indicated. Based on your knowledge of alkene addition reactions, explain this experimental result.arrow_forwardPeroxides are often added to free-radical reactions as initiators because the oxygen–oxygen bond cleaves homolytically rather easily. For example, the bond-dissociation enthalpy of the O¬O bond in hydrogen peroxide (H¬O¬O¬H) is only 213 kJ>mol (51 kcal>mol). Give a mechanism for the hydrogen peroxide-initiated reaction of cyclopentane with chlorine. The BDE for HO¬Cl is 210 kJ>mol (50 kcal>mol).arrow_forwardPropane reacts with Br2 to form 2-bromobutane in the presence of uv light. Produce the minor product of this reaction. Outline a down step-wise mechanism involving initiation, two propagation steps and two possible termination steps of the reaction. Give 3 isomers for 2-bromobutane. Name the 2 types of isomerism shown in Q3arrow_forward
- Organic ChemistryChemistryISBN:9781305580350Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. FootePublisher:Cengage Learning