Concept explainers
Interpretation: The addition of nucleophiles to the carbon-carbon double bond of an
Concept introduction:
Electrophilic addition reaction is an addition reaction where in a
Carbocation: The carbon ion that bears a positive charge on it.
Nucleophile: donates pair of electrons to positively charged substrate resulting in the formation of chemical bond.
Electrophile: accepts pair of electrons from negatively charged substrate results in chemical bond formation.
Consider elimination reaction where
The product of the elimination reaction is depends upon the β-positions of alkyl halide. If the β-positions are identical and the products formed are also identical. If the β-positions are different and the products formed are also different. This means the double bond can form in two different regions so this type of reaction is called regioselective and the products are called as regiochemical outcomes.
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Organic Chemistry
- Nonconjugated , -unsaturated ketones, such as 3-cyclohexenone, are in an acid-catalyzed equilibrium with their conjugated , -unsaturated isomers. Propose a mechanism for this isomerization.arrow_forward-Hydroxyketones and -hydroxyaldehydes are also oxidized by treatment with periodic acid. It is not the -hydroxyketone or aldehyde, however, that undergoes reaction with periodic acid, but the hydrate formed by addition of water to the carbonyl group of the -hydroxyketone or aldehyde. Write a mechanism for the oxidation of this -hydroxyaldehyde by HIO4.arrow_forwardAldehydes and ketones react with one molecule of an alcohol to form compounds called hemiacetals, in which there is one hydroxyl group and one ether-like group. Reaction of a hemiacetal with a second molecule of alcohol gives an acetal and a molecule of water. We study this reaction in Chapter 16. Draw structural formulas for the hemiacetal and acetal formed from these reagents. The stoichiometry of each reaction is given in the problem.arrow_forward
- For each of the transformations given below, draw the structures of the named starting material, products and possible intermediates. State the necessary reagents and conditions in the reaction scheme. More than one step may be required. cyclohexylmethanol ethenylbenzene pent-1-ene 2-methylpentan-3-ol cyclohexanecarbaldehyde acetophenone 2-methylpenta-2-amine propanoic acid + propanone a) b)arrow_forwardDetermine the structure of the methyl ester and organomagnesium bromide reagents that can be combined to form the following alcohol: Part 1: Draw the bond-line formula for the methyl ester reagent. Disregard stereochemistry. Part 2: Draw the bond-line formula for the organomagnesium bromide reagent. Disregard stereochemistry.arrow_forwardWhen 2-bromo-2-methylbutane is treated with a base, a mixture of 2-methyl-2-butene and 2-methyl-1- butene is produced. When potassium hydroxide is the base, 2-methyl-1-butene accounts for 45% of the product mixture. However, when potassium tert-butoxide is the base, 2-methyl-1-butene accounts for 70% of the product mixture. What percent of 2-methyl-1-butene would be in the mixture if potassium propoxide were the base? base Br A. Less than 45% B. C. 45% Between 45% and 70% D. More than 70%arrow_forward
- Identify by describing the structure of the products that will form when acid-catalyzed water is removed from trans-2-methyl cyclohexanol and sodium methoxide base and hydrogen bromide are removed from trans-1-bromo 4-methyl cyclohexane.arrow_forwardGive two sets of reactants (each set including an alkyl halide and a nucleophile) that could be used to synthesize the following ether:arrow_forwardAccount for the fact that 2-phenylpropanal is formed rather than its constitutional isomer, 1-phenyl-1-propanone.arrow_forward
- Draw the structure of the starting material needed to make 2-methylhept-3-yne using sodium amide in liquid ammonia, followed by 1-bromopropane. The starting hydrocarbon must have no more than five carbons 1) NaNH2, NH3() NaBr + 2) CHзCH2CH2Brarrow_forwardWrite a mechanism that accounts for the formation of ethyl isopropyl ether as one of the products in the following reaction. CI OEt HCI EtOH Write the mechanism for step one of this reaction. Show lone pairs and formal charges. Only the acidic hydrogen should be drawn out with a covalent bond. Write the mechanism for step two of this reaction (where the product of step one reacts with the solvent, ethanol). Show lone pairs and formal charges. Only the acidic hydrogen should be drawn out with a covalent bond. Write the mechanism for the last step of this reaction (formation of ethyl isopropyl ether). Show lone pairs and formal charges. Only the acidic hydrogen should be drawn out with a covalent bond. CI will act as the base in this reaction.arrow_forwardH₂C ཏཱཏི 1 ནི OH 1. Br2, PBг3 2. H₂O H3C OH Br The a-bromination of carbonyl compounds by Br2 in acetic acid is limited to aldehydes and ketones because acids, esters, and amides don't enolize to a sufficient extent. Carboxylic acids, however, can be a-brominated by first converting the carboxylic acid to an acid bromide by treatment with PBr3. Following enolization of the acid bromide, Br2 reacts in an a-substitution reaction. Hydrolysis of the acid bromide completes the reaction. Draw curved arrows to show the movement of electrons in this step of the mechanism. Arrow-pushing Instructions :0: H3C Br Br + :::OH2 Br H₂O H3C Br заarrow_forward
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