Concept explainers
a)
Interpretation:
- The rate determining step of the given reaction has to be predicted.
Concept Introduction:
Reactions of conjugated dienes:
An electrophilic addition reaction to a conjugated diene forms both
Kinetic and
Kinetic product: The more rapidly formed product is called the kinetic product. The reactions that produce the kinetic product as the major product are said to be kinetically controlled. The kinetic product predominates when the reaction is irreversible.
Thermodynamic product: The more stable product is called the thermodynamic product. The reactions that produce the thermodynamic product as the major product are said to be thermodynamically controlled. The thermodynamic product predominates when the reaction is reversible.
Rule: The stabilities of carbocation are,
b)
Interpretation:
- The product determining step of the given reaction has to be predicted.
Concept Introduction:
Reactions of conjugated dienes:
An electrophilic addition reaction to a conjugated diene forms both
Kinetic and thermodynamic products:
Kinetic product: The more rapidly formed product is called the kinetic product. The reactions that produce the kinetic product as the major product are said to be kinetically controlled. The kinetic product predominates when the reaction is irreversible.
Thermodynamic product: The more stable product is called the thermodynamic product. The reactions that produce the thermodynamic product as the major product are said to be thermodynamically controlled. The thermodynamic product predominates when the reaction is reversible.
Rule: The stabilities of carbocation are,
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Chapter 8 Solutions
CHEM 262 ORG CHEM EBOOK DIGITAL DELIVERY
- 1. Alkene Addition Reaction Mechanisms: Draw the product for the addition reactions below in the boxes. Then, draw the FULL electron-pushing mechanism for the reactions, including all intermediates (with formal charges and lone pairs of electrons) and all electron pushing arrows. For each step, label the electrophile and nucleophile and name what type of elementary step it is. a. Addition of H-Br to an alkene: of b. Addition of H₂O using an acid catalyst: H-CI: H-Ö-SO₂H (cat.) H₂Oarrow_forward1. Free radicals are generated by subjecting a molecule such as chlorine or bromine gas to A. high temperature conditions. B. photolysis. C. ionizing conditions. D. choices A and B 2. Which of the following radical intermediates is the most stable? q •CF3 A. B. C. D. 3. In the reaction shown below the intermediate that is formed at the fastest rate is Cl₂ A. uv CH, CH₂CHCH₂CH₂CH₂ B. CH, CH.CCH₂CH₂CH, CH₂ C. CH.CHCHCH.CH, D. CH₂ CH₂CHCH₂CHCHarrow_forwarda. How many monochlorination products can be obtained from the radical chlorination of methylcyclohexane? Disregard stereoisomers.b. Which product would be obtained in greatest yield? Explain.c. How many monochlorination products would be obtained if all stereoisomers are included?arrow_forward
- As we will learn in Section 13.12, many antioxidants–compounds that prevent unwanted radical oxidation reactions from occurring–are phenols, compounds that contain an OH group bonded directly to a benzene ring. a. Explain why homolysis of the O–H bond in phenol requires considerably less energy than homolysis of the O–H bond in ethanol (362 kJ/mol vs. 438 kJ/mol). b.Why is the C–O bond in phenol shorter than the C–O bond in ethanol?arrow_forwardDraw the products of the following reactions. Use curved arrows to show where the pair of electrons starts and where it ends up. a. ZnCl2 + CH3OH b. FeBr3 + Br c. AlCl3 + Cl−arrow_forwardAs we will learn in Section 15.12, many antioxidants-compounds that prevent unwanted radical oxidation reactions from occurring-are phenols, compounds that contain an OH group bonded directly to a benzene ring. a. Explain why homolysis of the O-H bond in phenol requires considerably less energy than homolysis of the O-H bond in ethanol (362 kJ/mol vs. 438 kJ/mol). b. Why is the C-O bond in phenol shorter than the C-O bond in ethanol? -O-H CH,CH2-0-H phenol ethanolarrow_forward
- 10. Draw an energy diagram for the addition of HBr to 1-pentene. Let one curve on your diagram show the formation of 1-bromopentane product and another curve on the same diagram show the formation of 2- bromopentane product. Draw and label the positions for all reactants, intermediates, and products. Which curve has the higher-energy carbocation intermediate? Which curve has the higher-energy first transition state?arrow_forwardA terminal alkyne (RC=CH) is exposed to excess HBr. What rule should be followed to determine the placement of the halogen atoms in the product? A. Markovnikov rule O B. Hofmann's rule O C. Zaitzev's rule D. Anti-Markovnikov rulearrow_forward10. In free-radical substitution reaction of alkanes with halogens under uv light, A. the photolytic breaking of the halogen is the rate determining step. B. the abstraction of hydrogen from alkane by the halogen radical is the rate determining step C. the formation of alkylradical is the rate determining step. D. the formation of halogen radical is the rate determining step. 11. Which of the following processes could be the termination step in free radical substitution reaction? A. C₂H6 ---→ 2CH3- B. C₂H6 +H --⇒ H₂ + C₂H5 C. CH3 + CH3 --→ C₂H6 D. C₂H5 --→ C₂H4 + Harrow_forward
- What is the relative rate of addition of HBr to A) 1,3-pentadiene, B) 1,4-pentadiene, and C) 1-pentyne? Oa. C> B> A Ob.B>A>C OC.C>A>B Od.A> B>Carrow_forward10. In free-radical substitution reaction of alkanes with halogens under uv light, A. the photolytic breaking of the halogen is the rate determining step. B. the abstraction of hydrogen from alkane by the halogen radical is the rate determining step C. the formation of alkylradical is the rate determining step. D. the formation of halogen radical is the rate determining step. 11. Which of the following processes could be the termination step in free radical substitution reaction? A. C₂H6 ---→ 2CH3 B. C₂H6 +H. --→ H₂ + C₂H5 C. CH3 + CH3 --→ C₂H₂ D. C₂H5 --→ C₂H4 + H 12. Which of the following is the most stable carbonium ion intermediate? A. primary carbonium ion B. secondary carbonium ion C. tertiary carbonium ion D. allyl carbonium ionarrow_forwardDraw the products obtained from the SN2 reaction of a. 2-bromobutane and methoxide ion. b. (R)-2-bromobutane and methoxide ion. c. (S)-3-chlorohexane and hydroxide ion. d. 3-iodopentane and hydroxide ion.arrow_forward
- Organic Chemistry: A Guided InquiryChemistryISBN:9780618974122Author:Andrei StraumanisPublisher:Cengage Learning
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