University:
Harrisburg University of Science and Technology
Course:
HEM 210 | Organic Chemistry I
Academic year:

2023
Views:

166

Pages:

10
Author:

Maverick Martin

Organic Chemistry Chapter 8 Reactions of Alkenes 1) Provide the structure of the major organic product of the reaction below. Answer: 2) Draw the major organic product generated in the reaction below. Pay particular attention to regio- and stereochemical detail. Answer: 3) Draw the major organic product generated in the reaction below. Pay particular attention to regio- and stereochemical detail. Answer: 4) HBr can be added to an alkene in the presence of peroxides (ROOR). What function does the peroxide serve in this reaction? A) nucleophile B) electrophile C) radical chain initiator D) acid catalyst E) solvent Answer: C 5) Predict the major product of the following reaction. A) B) C) D) Answer: B 6) Name the major product which results when HBr is added to 3-ethyl-3-hexene. Answer: 3-bromo-3-ethylhexane 7) Provide the structure of the major organic product of the reaction below. Answer: 8) Provide the major organic product of the reaction below. Answer: 9) Draw the major organic product generated in the reaction below. Pay particular attention to regio- and stereochemical detail. Answer: 10) Draw the major organic product generated in the reaction below. Pay particular attention to regio- and stereochemical detail. Answer: 11) Draw the major organic product generated in the reaction below. Pay particular attention to regio- and stereochemical detail. Answer: 12) Based on the relative stabilities of the intermediates involved, explain the basis for Markovinkov's rule in the addition of hydrogen halides to alkenes. Answer: The rate-determining step in this reaction is the production of a carbocation intermediate. Since this step is endothermic, Hammond's postulate allows one to gauge the relative stabilities of the transition states by comparing the relative stabilities of the carbocation intermediates. The reaction pathway which produces the more substituted carbocation will thus occur more rapidly. 13) Complete the following reaction and provide a detailed, step-by-step mechanism for the process. Answer: 14) When propylene reacts with hydrogen bromide in the presence of a peroxide initiator, which of the following structures are formed during the mechanism? A) B) C) D) H∙ Answer: B 15) Provide the structure of the major organic product of the reaction below. Answer: 16) Draw the major regioisomeric product generated in the reaction below. Answer: 17) Draw the major organic product generated in the reaction below. Pay particular attention to regio- and stereochemical detail. Answer: 18) Draw the major organic product generated in the reaction below. Pay particular attention to regio- and stereochemical detail. Answer: 19) Draw the major organic product generated in the reaction below. Pay particular attention to regio- and stereochemical detail. Answer: 20) Explain the regioselectivity observed in the radical addition of HBr to 2-methylpropene. Answer: The reaction proceeds via the addition of Br∙ to the alkene. Two competing pathways are possible, but the transition state leading to the more substituted alkyl radical is lower in energy. This process ultimately makes the addition anti-Markovnikov in nature.