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- 11. A radical cyclization cascade was used in the total synthesis of the natural product, hirsutene. Propose a mechanism for this transformation. Hints: a) Start by using the tin radical (left) to abstract the iodide. b) After both new rings are formed, an H atom can be abstracted from Bu3Sn–H to complete the mechanism.4) Draw the products following a radical bromination. Identify radicals, and draw resonance structures. Ph NBS/peroxide brominationd. HBr di-tert-butyl peroxide hv or A ndations of Organic Chemistry (Volume 1
- Rank the following radicals in order from least to most selective.| 1. Draw three resonance forms for the cyclohexadienyl radical Cyclohexadienyl radicalThe free-radical bromination of the following compound introduces bromine primarily at the benzylic position next to the aromatic ring. If the reaction stops at the monobromination stage, two stereoisomers result. Draw the two stereoisomers that result from monobromination at the benzylic position.
- The following molecules are subject to substitution (SN1 or SN2) reaction conditions. a) Identify if the leaving group (-Br) is attached to a 3°, 2°, 1°, or methyl Carbon. b) Rank the molecule with respect to their SN1 reactivity, with 1 being the fastest and 4 being the slowest. c) Rank the molecule with respect to their SN2 reactivity, with 1 being the fastest and 4 being the slowest. Br Br CH3B Br a. type of Carbon on C-Br b. SN1 reactivity (1 fastest, 4 slowest) c. SN2 reactivity (1 fastest, 4 slowest)8) Predict the two products that form in following Diels-Alder reaction. Circle the major product. CH₂O H O₂N CH₂OCH3 HModify the given copy of the starting material to draw the major radical bromination product(s), with close attention paid to the stereochemical outcome. If more than one stereoisomer is expected, then draw it.
- Allylic bromination of alkenes is accomplished with the reagent NBS (N-bromosuccinimide). The reaction proceeds by a radical chain mechanism. For the following reaction: NBS Br light, CCI4 a Select the species that you would expect to react in the first propagation step and draw curly arrows to show the mechanism. Use half-headed (fishhook) curved arrows to show electron reorganization. When drawing bond formation by pairing of single electrons, terminate the arrows in a hotspot located to one side of a reacting radical. This hotspot is not associated with any structural feature. Arrow-pushing Instructions 将一郎: Br H2 Previous Next6) 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 NBSThe reaction below gives two constitutional isomers as products. Draw the structure of the radical intermediate (including resonance structures), and of both products. NBS hv
