Concept explainers
(a)
Interpretation: The structure of the major organic product that would result from the reaction of
Concept introduction: Carbocation formation is relatively slower than acid-base reactions. Carbocations generated from
Analogous to the case that strong nucleophiles are more favored to react via
(b)
Interpretation: The structure of the major organic products that would result from the reaction of
Concept introduction:Carbocation formation is relatively slower than acid-base reactions. Carbocations generated from alkyl halides have two fates; they can be either trapped by nucleophiles to give substitution product or may deprotonate to yield a small amount of alkene. Stronger the base more is the probability of elimination over substitution over elimination. Further, if the still higher concentration is employed reaction proceeds via bimolecular elimination. On the other hand, the weak base waits until the carbocation is formed and the type of elimination with a relatively weak base is two-step elimination or
Analogous to the case that strong nucleophiles are more favored to react via
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Organic Chemistry: Structure and Function
- Describe the reaction mechanism for the hydrolysis of 2-bromo-2-methylpropane [CH3C(CH3)2Br] with aqueous hydroxide ions (OH-).arrow_forwardPure (S)-2-bromo-2-fluorobutane reacts with methoxide ion in methanol to give a mixture of (S)-2-fluoro-2-methoxybutane and three fluoroalkenes.(a) Use mechanisms to show which three fluoroalkenes are formedarrow_forwardb) Refer to the following equation to answer Q3b (i), (ii) and (iii). CH3 H,SO, Н—с—он C-CH3 ? + H2O Но- ČH3 (i) Determine the product of the above reaction. (ii) Name the above reaction. (iii) Propose the mechanism for the above reaction.arrow_forward
- Treatment of 2-bromo-2-methylbutane with KOH in ethanol yields a mixture of two Alkenes products. What are their likely structures? Show its mechanism.arrow_forward(b) Predict the suitable solvent (H2O or CH3COCH3) to increase the reaction of bromopropane (CH3CH2CH2B1) with sodium hydroxide (NaOH). Two reactions are shown below: NaOH, 55 °C CH;CH,CH,Br CH;CH,CH,OH + NaBr H,O (i) NaOH, 55 °C CH;CH,CH,Br CH;CH,CH,OH NaBr H,C CH (ii)arrow_forwardTwo substitution products result from the reaction between 3-chloro-3-methyl-1- butene with sodium acetate (CH3COO – Na +) in acetic acid under SN1. Identify the products.arrow_forward
- (а) Н (Б) Н (c) H Each of the monomers shown here can undergo free radical polymerization. For each polymerization: (i) Show the mechanism for the first two propagation steps, using benzoyl peroxide as the initiator. (ii) Draw the condensed formula for the polymer, showing the repeating unit. (iii) Provide a name for the polymer. H H H CI Hi c=0 H OCH3 H,N Vinylidene chloride Acrylamide Methyl vinyl etherarrow_forwardUnder milder temperatures than what is needed for dehydration, strong acids catalyze the self-condensation of 1-propyl alcohol to give di-n-propyl ether. The mechanism differs from that of today's reaction in that the protonated alcohol undergoes an Sn2 rather than an Sn1 reaction. Write the mechanism for the acid catalyzed condensation of ethyl alcohol to give diethyl ether. Make sure the mechanism includes protonation, Sn2, and deprotonation.arrow_forwardReaction of iodoethane with CN- yields a small amount of isonitrile, CH3CH2N≡C, along with the nitrile CH3CH2N≡N, as the major product. Write electron-dot structures for both products, assign formal charges as necessary, and propose mechanisms to account for their formation.arrow_forward
- The following sequence of steps converts (R)-2-octanol to (S)-2-octanol. Propose structural formulas for intermediates A and B, specify the configuration of each, and account for the inversion of configuration in this sequence.arrow_forwardNonconjugated , -unsaturated ketones, such as 3-cyclohexenone, are in an acid-catalyzed equilibrium with their conjugated , -unsaturated isomers. Propose a mechanism for this isomerization.arrow_forwardThe reaction below is the addition of HCl to 3-methylenecyclohex-1-ene. CH2 + HCI (i) Draw and name the kinetic and thermodynamic products structures of this reaction. (ii) Show the mechanism of reaction, while explaining the kinetic and thermodynamic preference of the reaction.arrow_forward
- Organic ChemistryChemistryISBN:9781305580350Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. FootePublisher:Cengage Learning