(a)
To draw: The resonance forms of three possible allylic intermediates that are formed during the reaction of NBS with
Interpretation: The resonance forms of three possible allylic intermediates that are formed during the reaction of NBS with
Concept introduction: The reaction that includes the addition of one or more bromine atoms in a compound is known as bromination reaction. Bromination reaction is a type of halogenation reaction. In this reaction, NBS (source of
A molecule that is uncharged and contains an unpaired electron is termed as free radical. Free radicals are highly reactive materials, but they have a short life span.
(b)
To determine: The ranking of three intermediates formed during the reaction of NBS with
Interpretation: The ranking of three intermediates formed during the reaction of NBS with
Concept introduction: The reaction that includes the addition of one or more bromine atoms in a compound is known as bromination reaction. Bromination reaction is a type of halogenation reaction. In this reaction, NBS (source of
A molecule that is uncharged and contains an unpaired electron is termed as free radical. Free radicals are highly reactive materials, but they have a short life span.
(c)
To draw: The products that are obtained from each of the free radical intermediate.
Interpretation: The products that are obtained from each of the free radical intermediate are to be drawn.
Concept introduction: The reaction that includes the addition of one or more bromine atoms in a compound is known as bromination reaction. Bromination reaction is a type of halogenation reaction. In this reaction NBS (source of
A molecule that is uncharged and contains an unpaired electron is termed as free radical. Free radicals are highly reactive materials, but they have short life span.
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Chapter 6 Solutions
Organic Chemistry (9th Edition)
- Photobromination reaction (Br₂/hv) is not particularly selective, minor structural isomeric products are also formed in addition to the major product. A. Assuming substitution of H for Br occurs at every possible kind of hydrogen atom (substitute only 1 H atom), draw all the isomeric product(s) can be formed for the two structures shown below. B. Indicate the major product in each case. C. Draw the critical radical intermediates that are involved in formation of the major product. x A Barrow_forward2. The bromination of 2-butene is an exergonic reaction. Br H3C. Br2 CH3 CH3 Br a. Draw the mechanism for the reaction (you may ignore the stereochemistry for this question). b. In the mechanism drawn above, identify any intermediates. C. How many transition states are involved in the above mechanism? Without drawing the transition state(s), indicate where they occur in the mechanism. d. Which of the following reaction co-ordinate diagrams best illustrates this reaction? Explain briefly. On the diagram, draw the structures of the reactants, products and intermediates at the correct locations on the diagram and indicate which position(s) correspond to the transition state(s). Page 18 of 19 EYRERIMENT 7: BROMINATION OF CINNAMIC ACID WINTER 2022arrow_forwardWhich of the following statements about an SN2 reaction is true? A. There are two transition states. B. There is one energy maximum. C. The transition state can be isolated and studied. D. For a carbon electrophile in the transition state, the hybridization of an sp3 carbon remains unchanged. E. The reaction rate does not depend on the concentration of the electrophile.arrow_forward
- SECTION 6: Show the mechanism of each reactions with arrows and intermediates form as in a. b. C. HBr Br₂ Cl₂, H₂O Br Br CI Br OHarrow_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_forwardDraw the most stable resonance form for the intermediate in the following electrophilic substitution reaction. Ⓒ. CCl₂ • You do not have to consider stereochemistry. . Include all valence lone pairs in your answer. . In cases where there is more than one answer, just draw one. Bo H₂SO4 First stage in synthesis of the insecticide DDT, which is now banned in the US #₂ SAIF CI OH CC13arrow_forward
- 19. Which of the following radical intermediates is the least stable? A. methane radical B. primary radical C. secondary radical D. tertiary radical 20. Compound J undergoes a carbonium ion rearrangement to yield compounds K and L. Based on the potential energy diagram below which of the following statements is TRUE. Potential energy A. K is formed faster and is more stable than L. B. K is formed faster and is less stable than L C. L is formed faster and is less stable than K L Reaction coordinate 21. Which of the following is the expected major product for the reaction below. 000 000 00-50 D. L is formed faster and is more stable than K D.arrow_forward1. 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_forwardHow many monochlorination products can be obtained from the radical chlorination of methylcyclohexane? Disregard stereoisomers. a. Which product would be obtained in greatest yield? Explain. b. How many monochlorination products would be obtained if all stereoisomers are included?arrow_forward
- Which chlorination product is formed via the lowest energy transition state in the rate-determining step? + CI-CI de .CI O All radical chlorinations require the same activation energies.arrow_forward6) Write the mechanism (two propagation steps only, starting with the bromine radical in the first step and using Br2 in the second step) and that would explain how the following two products are produced. (Hint – the allylic radical is resonance stabilized.) Br Br NBSarrow_forwardited Draw both resonance structures of the most stable carbocation intermediate in the reaction shown. od m... • You do not have to consider stereochemistry. . Do not include anionic counter-ions, e.g., I', in your answer. • Draw one structure per sketcher. Add additional sketchers using the drop-down menu in the bottom Separate resonance structures using the → symbol from the drop-down menu. ● CH4 + ? HBrarrow_forward
Organic Chemistry: A Guided InquiryChemistryISBN:9780618974122Author:Andrei StraumanisPublisher:Cengage Learning