Concept explainers
Interpretation:
The given
Concept introduction:
The nucleophilic substitution reactions are the reactions in which one nucleophile is substituted by another nucleophile. These reactions depend upon the nucleophilicity and concentration of the nucleophile. The
Stereochemistry is the study of the different types of
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Chapter 17 Solutions
Organic Chemistry
- The addition of water to aldehydes and ketones occurs rapidly, although it is not thermodynamically favored. What would be the product for the reaction above? Hint: Think of the self-ionization of water and the polarity of the carbonyl group.arrow_forwardExplain with the help of electronic effects, ‘generally haloalkenes undergo nucleophilic substitution reactions whereas haloarenes undergo electrophilic substitution reactionarrow_forwardWhich of the following is true regarding the Heck coupling reaction? 1)Bond formation can occur between an aryl halide and an alkene in the presence of a palladium-ligand catalyst. 2)Two carboxylic acid derivatives can be linked together in the presence of a palladium-ligand catalyst 3)An alkene and alcohol are linked together in the presence of a palladium-ligand catalyst. 4)Two alkenes can be linked together in the presence of a palladium-ligand catalyst.arrow_forward
- Provide structure(s) for the starting material(s), reagent(s) or the major organic product(s) of each of the following reactions.arrow_forwardAlkyl halides undergo nucleophilic substitution and elimination reactions. When the kinetics of the reaction are measured, if the rate of the reaction is found to be dependent only upon the concentration of the alkyl halide the reaction is first order. The substitution reaction is thus termed SN1, and the elimination reaction is termed E1. These reactions are unimolecular and occur in two steps. The first step is rate-limiting and involves the loss of the leaving group to form a carbocation. In the second, fast, step the nucleophile adds to the carbocation in the SN1 reaction or elimination occurs to give an alkene in the E1 reaction. Because the carbocation is planar, the nucleophile can add to either face and therefore racemization is usually observed although solvent effects can influence this somewhat. E1 elimination follows Zaitsev’s rule and typically yields the most substituted alkene as the major product. Conditions which favor the SN1/E1 pathway include the use of a weak…arrow_forwardAlkyl halides undergo nucleophilic substitution and elimination reactions. When the kinetics of the reaction are measured, if the rate of the reaction is found to be dependent only upon the concentration of the alkyl halide the reaction is first order. The substitution reaction is thus termed SN1, and the elimination reaction is termed E1. These reactions are unimolecular and occur in two steps. The first step is rate-limiting and involves the loss of the leaving group to form a carbocation. In the second, fast, step the nucleophile adds to the carbocation in the SN1 reaction or elimination occurs to give an alkene in the E1 reaction. Because the carbocation is planar, the nucleophile can add to either face and therefore racemization is usually observed although solvent effects can influence this somewhat. E1 elimination follows Zaitsev’s rule and typically yields the most substituted alkene as the major product. Conditions which favor the SN1/E1 pathway include the use of a weak…arrow_forward
- 3-Chloro-2-methylpropene reacts with sodium methoxide in methanol to form 3-methoxy-2-methylpropene. For each of the following changes in the reaction conditions, state whether the reaction rate would increase, decrease, or remain the same. Explain your reasoning. In some cases the identity of the major organic product would be expected to change; in such cases, give the expected major product. (a) the same quantities of reagents are dissolved in half the volume of methanol (b) 3-bromo-2-methylpropene is used in place of 3-chloro-2-methylpropene (c) sodium methanethiolate (CH3SNa) is used in place of of sodium methoxidearrow_forwardExplain with the help of electronic effects, ‘generally haloalkenes undergo nucleophilic substitution reactions whereas haloarenes undergo electrophilic substitution reactions’.arrow_forwardAlkynes 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 -X티 Hö: H-O -CH3 -CH3 H30*arrow_forward
- Write the mechanism, as well as the structure of intermediate A and product B, for the following reaction.arrow_forward3-Chloro-2-methylpropene reacts with sodium methoxide in methanol to form 3-methoxy-2-methylpropene. For each of the following changes in the reaction conditions, state whether the reaction rate would increase, decrease, or remain the same. Explain your reasoning. In some cases the identity of the major organic product would be expected to change; in such cases, give the expected major product. (a) dimethyl sulfoxide (DMSO) is used in place of methanol (b) methanol is used by itself without sodium methoxide (c) 1-chloro-2,2,-dimethylpropane is used in place of 3-chloro-2-methylpropenearrow_forwardWhat elimination side reaction can occur from the following reaction in the presence of sulfuric acid? HINT: The product is an alkene but not 1-butene and the reaction has more than one step.arrow_forward
- Organic ChemistryChemistryISBN:9781305580350Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. FootePublisher:Cengage LearningChemistry for Today: General, Organic, and Bioche...ChemistryISBN:9781305960060Author:Spencer L. Seager, Michael R. Slabaugh, Maren S. HansenPublisher:Cengage Learning