Concept explainers
Interpretation: Poor selectivity in the formation of the brominated products when equimolar mixture of
Concept introduction: The monobromination performed with ultraviolet light proceeds via radical chain mechanism.
In general, tertiary
The phenomenon of hyperconjugation refers to donation of
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Organic Chemistry: Structure and Function
- Following is a balanced equation for the allylic bromination of propene. CH2==CHCH3 + Br2 h CH2==CHCH2Br + HBr (a) Calculate the heat of reaction, H 0, for this conversion. (b) Propose a pair of chain propagation steps and show that they add up to the observed stoichiometry. (c) Calculate the H 0 for each chain propagation step and show that they add up to the observed H 0 for the overall reaction.arrow_forwardCH3 CH3 Br- Br2 CH2CI2 CH3 CH3 H3C H3C Br 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 CH2C12. 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 Br- .CH3 .CH3 H3C H3C :Br :Br:arrow_forward4. What are the products obtained from the following elimination reaction? Indicate the major product. CH3 CH,CH,ČCH, H2O 5. a) Determine the major product that is formed when the alkyl halide reacts with a hydroxide ion in an elimination reaction. CH;CH,CH,CH,CCH, Br b) For the major elimination product obtained in 5a), which stereoisomer (cis or trans) is obtained in greater yield? Draw the two isomers and provide the names of the compounds.arrow_forward
- Draw the major organic product of the reaction shown below. + PBr3 OH • You do not have to consider stereochemistry. • You do not have to explicitly draw H atoms. Aarrow_forwardDraw a structural formula for the major organic product of the reaction shown below. ● ● ● ● Br MAX. + [(CH3)3C]2CuLi Consider E/Z stereochemistry of alkenes. Do not show stereochemistry in other cases. You do not have to explicitly draw H atoms. Do not include organocopper or inorganic ion by-products in your answer. #[ ] در ? ChemDoodle Ⓡarrow_forwardDraw the structure of the major organic product of the reaction below. ● + CHCI3 MILL KOH Use the wedge/hash bond tools to indicate stereochemistry where it exists. Show stereochemistry in a meso compound. If the reaction produces a racemic mixture, just draw one stereoisomer. ▼ n [F ? ChemDoodleⓇarrow_forward
- CH3 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_forward4) Fill in the appropriate starting materials, reagents or products in the following reactions. OH / AIC13 NO₂ Y CI / AICI,arrow_forwardSelect the possible major product in the given reaction. 41. Dehydration of alcohols 42. Elimination of H-X in alkylhalides 43. Reaction of alcohols and carboxylic acids 44. Reduction of aldehydes 45. Substitution of reaction between ROH and SOCI, Choices: (A) 1 ROH (B) 2 ROH (C) 3 ROH (D) Alkene RCHO (E) (AB) RCOOH (AC) RCOR' (AD) RX Which of the following reagent (s) are needed in the following reactions? 46. Reduction of carboxylic acids to primary alcohols 47. Oxidation of primary alcohols to aldehydes 48. Reduction of ketones to secondary alcohols 49. Saponification of esters 50. Dehydration of alcohols Choices: aqueous NAOH and heat (B) Hạ in Pt (C) (A) H;O, H;SO, (D) H,SO, with heat (E) K,Cr,O, and H,So, (АB) LIAIH, (AC) PCC (AD) Tollens' reagentarrow_forward
- 2. How many monochlorinated products will form from each of the following? Draw them and identify the most stable one. Also, include the reagent used for the monochloronation reaction. C 1 Ctrarrow_forwardDraw the structure of the major organic product of the reaction below. CH₂ + CHCI 3 KOH Use the wedge/hash bond tools to indicate stereochemistry where it exists. Show stereochemistry in a meso compound. If the reaction produces a racemic mixture, just draw one stereoisomer. O. #[ ] در ? ChemDoodleⓇarrow_forwardStep 4a: Classify step. The target product is present, but the reaction is not over. The ethoxide ion has been regenerated. :0: :0: What is the key process in the next step of the mechanism? proton transfer formation of a o bond between nucleophile and electrophile loss of a leaving group carbocation rearrangement (e.g., methyl or hydride shift)arrow_forward
- Organic ChemistryChemistryISBN:9781305580350Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. FootePublisher:Cengage Learning