Concept explainers
Interpretation:
The equation including the curved arrows that best represents the rate determining step in the mechanism is to written.
Concept Introduction:
The slowest step in the substitution reaction is the rate determining step.
For the substitution reactions by an
Thus,
Curved arrows indicate the movement of electrons in a mechanism.
Primary carbocations are not stable and so, they do not form as a carbocation intermediate in a given mechanism.
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- In two parts, outline the Electrophilic aromatic substitution for the nitration of benzene using nitric acid and sulfuric acid: A) In part I, using the curved arrow formalism, outline a mechanism for the formation of the nitronium ion, NO2+ starting from nitric acid, HNO3 and sulfuric acid, H2SO4. Do not forget to show all of the formal charges for each atom that is not zero in this mechanism. B) Starting from the nitronium ion that you generated in part “a” from above, outline the Electrophilic Aromatic Substitution of this ion with benzene.arrow_forwardConversion of an alkene to a halohydrin and internal displacement of a halide ion by an alkoxide ion are both stereoselective. Use this information to demonstrate that the configuration of the alkene is preserved in the epoxide. As an illustration, show that reaction of cis-2-butene by this two-step sequence gives cis-2,3- dimethyloxirane (cis-2-butene oxide).arrow_forwardWorking Backwards Parte Deux. a.First, identify which functional groups changed during the reaction. Did stereochemistry change too? b. Based on your answers to A and B, what kind of reaction occurred here, SN1 or SN2? c.Suggest reagents and solvent that could accomplish this reaction.arrow_forward
- State the characteristic of the SN2 and SN1 mechanism towards alkyl halide compounds based onmolecularity, reaction rate constant, formation of product(s), reactivity of alkyl halides and thestrength of nucleophile.arrow_forwardwe know that ethers, such as diethyl ether and tetrahydrofuran, are quite resistant to the action of dilute acids and require hot concentrated HI or HBr for cleavage. However, acetals in which two ether groups are linked to the same carbon undergo hydrolysis readily, even in dilute aqueous acid. How do you account for this marked difference in chemical reactivity toward dilute aqueous acid between ethers and acetals?arrow_forwardIn the chemical reaction between 1-Bromobutane and ethanolic silver nitrate solution, a precipitate is barely formed. Using the skeletal structures of the molecules, write out the skeletal structure of each reaction (don't include the mechanism). Identify what the nucleophile is in each type of reaction, especially the SN1 reaction. Explain the reactivity of each electrophile/substrate in terms of whether they are tertiary, secondary, primary, etc. for each reaction. Include the overall chemical reaction.arrow_forward
- Understanding different substitution and elimination pathways gives useful insight into chemical mechanisms and pathways. Give the different important aspects of the Sn1, Sn2, E1, E2, and E2cB reactions.arrow_forwardThe 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_forwardCan you answer this question regarding this procedure: Discuss the Sn1 mechanism and then summarize how the different conditions impacted the rate. Look at leaving group, solvent, and substitution. What trends did you observe? Did any of the results turn out differently than you had expected? Do you think this is because of the mechanism or because of practical issues? Suggest possible ways to improve on the rate study for future trials.arrow_forward
- Write the synthesis of the target compounds by starting from each benzene given in the following options and by writing the mechanism of each step separately.arrow_forwardQuestion: How do quantum mechanical effects influence the stability and reactivity of molecules with non-classical carbocations, such as the 2-norbornyl cation, and how does this impact the reaction mechanisms and outcomes?arrow_forwardThese are the following alkyl halides. State and explain whether these four molecules would undergo substitution for an Sn1 mechanism or Sn2. Explain your answer.arrow_forward
- Organic Chemistry: A Guided InquiryChemistryISBN:9780618974122Author:Andrei StraumanisPublisher:Cengage Learning