Concept explainers
Interpretation:
The chain reaction mechanism for the formation of
Concept introduction:
Radical halogenation is the reaction in which hydrogen atoms of
At normal temperature and pressure, chlorine and methane do not react with each other. The reaction is initiated by light or heat. When exposed to light,
The reaction that is initiated by light is more efficient because a very small amount of light photons allows a large number of products to be formed.
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ORGANIC CHEM. VOL.1+2-W/WILEYPLUS
- 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) 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_forward9. (a) Under certain conditions, the reaction of 0.5 M 1-bromobutane with 1.0 M sodium methoxide forms 1-methoxybutane at a rate of 0.05 mol/L per second. What would be the rate if 0.1 M 1-bromobutane and 2.0 M NaOCH3 were used? (b) Consider the reaction of 1-bromobutane with a large excess of ammonia (NH3). Draw the reactants, the transition state, and the products. Note that the initial product is the salt of an amine (RNH* Br) which is deprotonated by the excess ammonia to give the amine. (c) Show another SN2 reaction using a different combination of an alkoxide and an alkyl bromide that also produces 1-methoxybutane.arrow_forward3-Chloro-1-butene reacts with sodium ethoxide in ethanol to produce 3-ethoxy-1- butene. The reaction is second order, first order in 3-chloro-1-butene, and first order in sodium ethoxide. In the absence of sodium ethoxide, 3-chloro-1-butene reacts with ethanol to produce both 3-ethoxy-1-butene and 1-ethoxy-2-butene. Explain these results.arrow_forward
- Answer the following questions regarding the nucleophilic substitution reaction shown below: CH3CH2CH2-Br + I- ------> CH3CH2CH2I + Br- (a) Write the rate law for this reaction assuming that it is a one step reaction that is first order in each of the reactants. (b) Holding the concentration of the iodide ion constant, what change would be observed in the rate if the concentration of the n- propyl bromide was tripled? (b) Assume that this is an exothermic reaction, draw the energy profile and identify the location of the transition state. (c) Draw the transition state for this reaction. (d) What change is observed for the entropy of the system during this reaction? (e) Show the likely mechanism of this reaction using the proper curved arrowsarrow_forwardEthane reacts with chlorine (Cl2) in the presence of ultra-violet (UV) light, to produce 1-chloropropane (CH3CH2Cl) and hydrogen bromide (HCl). As shown in the equation below.CH3CH3+ Cl2→ CH3CH2Cl+ HClDescribe the reaction mechanism of the reaction between ethane and chlorine to produce 1-chloroethane. The description should be detailed and must include the type of bond fission that takes place. You may sketch and insert suitable diagrams to aid your description if you wish.arrow_forwardImagine that phenol (“hydroxybenzene”) and nitrobenzene are reacted (in separate beakers) with a hot solution containing both concentrated sulfuric acid and concentrated nitric acid. A) Phenol reacts much more quickly than benzene, and benzene reacts much more quickly that nitrobenzene. Explain this observation, using at least one appropriate reaction coordinate diagram as part of your answer (be sure to label your reaction diagram with appropriate structures). You do not need to include any complete mechanisms, but you may wish to use portions of mechanisms as part of your discussion.arrow_forward
- (a) Give the names of reagents and conditions for each of the reactions I and IIarrow_forward4) Provide a complete step by step mechanism for the following reactions. + HCC13 Peroxide, Joubong sitwa CC13arrow_forwardConcentrated phosphoric acid and concentrated sulfuric acid are common choices for dehydrating alcohols. Concentrated hydrochloric acid is not. What problem might occur if concentrated hydrochloric acid were substituted for phosphoric acid in the cyclohexene synthesis? allylic chlorination of the cyclohexene product may occur chlorocyclohexane may form as a byproduct the equilibrium will now favor formation of cyclohexanol by Le Chatelier's Principle hydrochloric acid is a weaker acid than phosphoric acidarrow_forward
- Imagine that phenol (“hydroxybenzene”) and nitrobenzene are reacted (in separate beakers) with a hot solution containing both concentrated sulfuric acid and concentrated nitric acid. A) In analyzing the products, you discover that the substitution pattern resulting from the reaction with phenol differs from the reaction with nitrobenzene. Explain this difference in substitution patterns using one or more judiciously selected reaction mechanisms or portions of mechanisms.arrow_forwardFree‑radical halogenation can occur with chlorine and a source of direct UV radiation or sunlight. Chlorination of 2,4‑dimethylpentane via radical halogenation leads to the formation of all three of the products shown. Estimate the relative percentages of each product that will be formed using this means of halogenation. Presume that 1 equivalent of chlorine is used.arrow_forwardBromine reacts with alkenes in methanol according to the equation (see image 1). When this reaction was carried out with 4-tert-butylcyclohexene, only one isomer was formed with the molecular formula C12H23BrO (80% yield) a) Which of the following is the structure more reasonable for this compound? (see image 2) b) Explain your reasoning through a corresponding mechanismarrow_forward
- Organic ChemistryChemistryISBN:9781305580350Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. FootePublisher:Cengage Learning