Interpretation:
The outcome of the reaction of tert-pentylchloride with propene and its mechanistic steps are to be predicted.
Concept introduction:
Electrophiles are electron-deficient species, which has positive or partially positive charge. Lewis acids are electrophiles, which accept electron pair.
Nucleophiles are electron-rich species, which has negative or partially negative charge. Lewis bases are nucleophiles, which donate electron pair.
Substitution reaction: A reaction in which one of the hydrogen atoms of a hydrocarbon or a
Elimination reaction: A reaction in which two substituent groups are detached and a double bond is formed is called elimination reaction.
Addition reaction: It is the reaction in which unsaturated bonds are converted to saturated molecules by the addition of molecules.
Carbocation is a molecule having a carbon atom bearing three bonds and a positive formal charge.
Carbocation are generally unstable because they do not have eight electrons to satisfy the octet rule.
The order of stability of carbocation is such that the tertiary carbocation is the most stable whereas the primary carbocation is the least stable, and secondary carbocation lies between primary and tertiary carbocations.
If primary carbocation is obtained in product, it rearranges itself to secondary or tertiary carbocation to form more stable product.
If secondary carbocation is obtained in product, it rearranges itself to tertiary carbocation to form more stable product.
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Organic Chemistry
- When the given reactions below are done once, which of the following reactions is used to prepare dihalogenated alkyl halides as major products? Select one: O Reaction of ethane with Cl₂ in the presence of light Reaction of ethene with HBr Reaction of ethyne with two moles of HCI Reaction of ethene with Br₂ in H₂Oarrow_forward6) 25pts. Draw the structure of the major alkene product (or products) formed by treatment of each of the following haloalkanes with sodium ethoxide in ethanol. Assume the mechanism is E2 elimination. t-BuO K t-BUOH Br CH3 Eto Na F ETOH CH2CH3 CI H- Eto Na -CH2CH3 ELOH H- ČH3 Br Eto Na ELOH CH3 CI, H Eto Na CH2CH3 H3C H D ELOHarrow_forwardElimination of HBr from 2-bromobutane affords a mixture of 1-butene and 2-butene. With sodium ethoxide as base, 2-butene constitutes 81% of the alkene products, but with potassium tert-butoxide, 2-butene constitutes only 67% of the alkene products. Offer an explanation for this difference.arrow_forward
- Provide a series of synthetic steps by which (CH3)2C CH2 could be prepared from 2-methylpropane.arrow_forwardWhen 2-iodo-1,4-dimethylcyclohexane is heated in acetic acid, CH3COOH, a mixture of substitution and elimination products is obtained. Provide structures for all possible products, writing [not drawing] the name of the mechanism by which each one is formed.arrow_forwardC=CH H20, H2SO4 H9SO4 CH3 Alkynes do not react directly with aqueous acid as do alkenes, but will do so in the presence of mercury(II) sulfate as a Lewis acid catalyst. The reaction occurs with Markovnikov regiochemistry, so the OH group adds to the more highly substituted carbon and the H adds to the less highly substituted carbon. The initial product of the reaction is a vinyl alcohol, also called an enol. The enol immediately rearranges to a more stable ketone via tautomerization. Draw curved arrows to show the movement of electrons in this step of the mechanism. Arrow-pushing Instructions H-OH HO: Hjö: C=CH c=CH Hö Hg Hgarrow_forward
- An alkene having the molecular formula C,H12 is treated sequentially with ozone (O3) and zinc/acetic acid to give the product/s shown. CH3CH2CH,CH½CH2CH Draw a structural formula for the alkene. You do not have to consider stereochemistry. You do not have to explicitly draw H atoms. • In cases where there is more than one answer, just draw one. P opy aste Previous Nextarrow_forwardAlkylation of benzene with 1-chlorobutane in the presence of AlCl3 gave not only the expected butylbenzene product but also, as a major product, (1-methylpropyl)benzene. Write an equation for the reaction Propose a mechanism to account for the formation of butylbenzene Propose a mechanism to account for the formation of (1-methylpropyl)benzenearrow_forwardIf phenoxide ion is allowed to react with 1-bromopentane, pentyl phenyl ether is obtained. However, if cyclohexane is used as the alkyl halide, the major products are phenol and cyclohexene. Explain how these products were formed.arrow_forward
- In an attempt to prepare propylbenzene, a chemist alkylated benzene with 1-chloropropane and aluminum chloride. However, two isomeric hydrocarbons were obtained in the proportion of 2: 1. What is the main product? How did this come about? Explain showing the mechanism and nomenclature of the reaction compoundsarrow_forwardWhen the alkene A was treated first with Hg(OAc)2 in MeOH and second with NaBH4 the product was the ether B. Using curved arrows please give the mechanism for the first step of (Hg(OAc)2 in MeOH) this reaction, including any regioselectivity or stereoselectivity. H3C 1. Hg(OAc)2, MeOH H3C O-CH3 =CH2 ✓ -CH3 H3C 2. NaBH H3C A Barrow_forwardCCH H20, H2SO4 H9SO4 CH3 Alkynes do not react directly with aqueous acid as do alkenes, but will do so in the presence of mercury(II) sulfate as a Lewis acid catalyst. The reaction occurs with Markovnikov regiochemistry, so the OH group adds to the more highly substituted carbon and the H adds to the less highly substituted carbon. The initial product of the reaction is a vinyl alcohol, also called an enol. The enol immediately rearranges to a more stable ketone via tautomerization. Draw curved arrows to show the movement of electrons in this step of the mechanism. Arrow-pushing Instructions Hjö: -CH3 -CH3 H3O*arrow_forward
- Organic ChemistryChemistryISBN:9781305580350Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. FootePublisher:Cengage Learning