Concept explainers
Interpretation:
For the given reaction that produces both substitution and elimination products at room temperature, it is be determined which product will be the major product if the temperature at which the reaction is run is raised and which product will be the major product if the temperature of the reaction is lowered.
Concept introduction:
Most of the reaction often produces both substitution as well as elimination products. When substitution and elimination reactions are both favored under a specific temperature, it is often possible to change the outcome by changing the temperature under which the reactions are carried out. Substitution and elimination products are formed in roughly equal amounts at the lower temperatures. Increasing the temperature of the reaction tends to promote elimination more than substitution because there is significantly more disorder in the products of an elimination reaction than in the products of a competing substitution reaction.
Want to see the full answer?
Check out a sample textbook solutionChapter 9 Solutions
Organic Chemistry: Principles And Mechanisms: Study Guide/solutions Manual (second)
- For the hydrolysis reaction of a nitrile with H30*, H30*, which of the following is produced intermediately. O Amide O Amine O Amine and acid O Amide and acidarrow_forwardCH3 CH3 Br- Br2 .CH3 CH2Cl2 CH3 H3C H3C Br Electrophilic addition of bromine, Brɔ, to alkenes yields a 1,2-dibromoalkane. The reaction proceeds through a cyclic intermediate known as a bromonium ion. The reaction occurs in an anhydrous solvent such as CH,Cl,. In the second step of the reaction, bromide is the nucleophile and attacks at one of the carbons of the bromonium ion to yield the product. Due to steric clashes, the bromide ion always attacks the carbon from the opposite face of the bromonium ion so that a product with anti stereochemistry is formed. Draw curved arrows to show the movement of electrons in this step of the mechanism. Arrow-pushing Instructions CH3 CH3 CH3 CH3 H3C H3C :Br: :Br:arrow_forwardH3C CH3 H3C NA C→XT Br Br₂ CH₂Cl₂ H3C Electrophilic addition of bromine, Br₂, to alkenes yields a 1,2-dibromoalkane. The reaction proceeds through a cyclic intermediate known as a bromonium ion. The reaction occurs in an anhydrous solvent such as CH₂Cl₂. CH3 Br In the second step of the reaction, bromide is the nucleophile and attacks at one of the carbons of the bromonium ion to yield the product. Due to steric clashes, the bromide ion always attacks the carbon from the opposite face of the bromonium ion so that a product with anti stereochemistry is formed. Draw curved arrows to show the movement of electrons in this step of the mechanism. Arrow-pushing Instructions Br CH3 H3C CH3arrow_forward
- In free-radical substitution reaction of alkanes with halogens under uv light, the photolytic breaking of the halogen is the rate determining step. the formation of alkylradical is the rate determining step. the formation of halogen radical is the rate determining step. the abstraction of hydrogen from alkane by the halogen radical is the rate determining steparrow_forwardSome elimination reactions can undergo cation rearrangements. Given the following reaction conditions, draw three possible elimination products that could form with carbocation rearrangement, or without carbocation rearrangment. Include major and minor products. Br Weak Basearrow_forwardWhich is true of a free energy diagram for an SN1 eaction? It shows one transition state. It always shows that the reaction is net exothermic. It never shows intermediates. It always shows that the reaction is net endothermic. It always includes multiple energy barriers.arrow_forward
- 4. A CHEM 245 student wants to synthesize some ethylene glycol to use as antifreeze in his radiator this winter. He proposes the following reaction to his instructor, who quickly explains that this reaction won't work as proposed due to the student's choice of reagent. 1) NaH 2) H20 OH Но a) Why can't sodium hydride (NaH) be used as the nucleophile in the reaction above? b) Propose an alternate reagent that COULD be used with the ethylene oxide to successfully give the desired ethylene glycol product.arrow_forwardAll this worksheet asks for are the major substitution products and the major elimination products, please help me!arrow_forwardFor the trans isomer of cinnamic acid: o Draw the structure of the trans isomer of cinnamic acid and the structure of the intermediate bromonium ion. Note that the bromonium ion can exist as two enantiomeric forms. You should draw both of these isomeric forms. o Draw the structures of the two dibrominated products which can form when a bromide ion adds to the bromonium ion intermediate. These must be drawn to show the correct stereochemistry. Assign the chiral carbons as R or S.arrow_forward
- Tell which of these transformations are oxidations and which are reductions based on whether there is addition or removal of O or H.arrow_forwardOnly one of the chlorine atoms in the molecule, 3,4-dichloronitrobenzene, will undergo nucleophilic substitution. Indicate which position will react and provide the expected product for the given reaction using reaction intermediates (resonance structures).arrow_forwardThe reaction of methylpropene with HBr in ether gives one of the two products below as the major product. Br HBr Br ether Product A Product B Product would have a higher energy transition state for the formation of the intermediate leading to it. O A O B O Both products would have the same transition state.arrow_forward
- Organic Chemistry: A Guided InquiryChemistryISBN:9780618974122Author:Andrei StraumanisPublisher:Cengage LearningOrganic ChemistryChemistryISBN:9781305580350Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. FootePublisher:Cengage Learning
- Chemistry for Today: General, Organic, and Bioche...ChemistryISBN:9781305960060Author:Spencer L. Seager, Michael R. Slabaugh, Maren S. HansenPublisher:Cengage LearningEBK A SMALL SCALE APPROACH TO ORGANIC LChemistryISBN:9781305446021Author:LampmanPublisher:CENGAGE LEARNING - CONSIGNMENT