In cationic rearrangements like the pinacol reaction, migrating hydrogens and alkyl groups are shown moving in one step from carbon to carbon as pictured below. This reaction is also classified as a [1,2]-sigmatropic rearrangement. R R R -C+-R R .C+ -R OH R OH R But for migration of phenyl groups (benzene rings), the rearrangement proceeds by a two step process as pictured below: R C+ -R R OH R он R H -R R-C+ OH R -R Relative the to benzene ring and considering the center intermediate, phenyl migration is a(n) a. acyl substitution b. SN2 c. nucleophilic aromatic d. benzyne e. free radical f. electrophilic aromatic g. carbonyl h. SN1 Clear my choice substitution?
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- 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:Draw the structure(s) of the major organic product(s) of the following reaction. CH3 0 N-C=C H + CH3-C-CI CH3 1. in ether 2. NaHCO3 / H₂O Draw the structure(s) of the major organic product(s) of the following reaction مل CEN 1. ethanol / reflux 2. aqueous HCIWhat is the expected major product of the reaction sequence shown? Assume standard workup after each step and that only the major product of the first step is taken on to the second step. OH 1. PBR3 H3C/,, 2. NaOEt, EtOH Br H3C,, OEt
- app.101edu.co Draw the major product of this reaction. Ignore inorganic byproducts. Assume that the water side product is continuously removed to drive the reaction toward products. esc F1 CH3CH2CH2OH H2SO4 (cat), heat ☀ F2 80 F3 OH a F4 W Q F5 Atoms and P Draw or ta MacBook A C F610. Terpene is a class of naturally occurring molecules, found in many essential oils from plants, that share the same alkene features. All terpenes have a similar 5 carbon unit that includes an alkene thought to be biologically synthesized from the molecule isoprene. All terpenes are biosynthesized from molecules with the good leaving group: pyrophosphate (OPP). Loss of this OPP leads to the formation of a resonance stabilized carbocation. The new carbocation can undergo a nucleophilic attack from a T-bond as seen in acid-catalyzed hydration and hydrohalogenation, forming a new carbocation. This new carbocation can undergo an E1 reaction to form a new alkene. Add the curved arrows of the following reaction. hopp COPP D 5 R-carvone (spearmint oil) - Q Search 40 6 & COPP 1 COPP COPPWhat is the organic product formed in the following sequence of reactions? Br (1) Mg/ether, (2) CO₂ HOCH₂/H* (1) DIBAL-H, toluene, -78°C heat (2) H*(aq) (3) H*(aq) II H III IV de "a H H I ?
- IV. Complete the equations for the following reactions. Show all organic alkene products form, mechanism, indicate the major product and the rule Ş(CH3)2 NaSH HEAT OH™ HEAT9. Hydrates, in which two -OH groups are connected to the same carbon, are not favorable except in a few cases. One case is: a) acetaldehyde c) acetone b) formaldehyde d) chloroform 10. The Wolff-Kishner reaction, in which an aldehyde or ketone is treated with NH2NH2 and KOH, is: a) an oxidation c) an SN2 reaction b) a reduction d) a hydration 11. Which of these is most likely to dissolve in 5% NaOH? a) 1-decanol b) decanal c) decanoic acid d) 2-decanone bu itcolf Draw tbe20. Identify the product for each step in the following reaction sequence. Write complete equations showing the structure of all reactants and products for each step. (a) Isopropyl benzene + NBS/heat ---------->A (b) A+ t-BuOK ---------> B (c) B + 1)BH3 followed by 2)H2O2/NaOH -----> C (d) C + PCC ------> D
- 8. Draw a reaction coordinate diagram depicting the thermodynamics of the following reaction. Indicate the locations of any starting materials, intermediates, products, transition states, free energy of reaction and activation energy present in the diagram. Draw the transition state structure, complete with charge information, for the following transformation. Br H₂CCH₂H 20 CA CH3 H3CCH2OH + H CH3 CH3 + BI-H3C CH3 H3C NA C→XT Br Br₂ CH₂Cl₂ H3C 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 CH₂Cl₂. CH3 Br 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 Br CH3 H3C CH3Must show your work to get full credit 1. Write the structures of all the dehydration products (including E and Z isomers) that might be obtained from the reaction shown below: 4. *os'H Heat Но 2. Write the structure of the key intermediate and the product (with correct stereochemistry) for the reaction of N-Bromosuccinimide (NBS) with cyclopentene in aqueous DMSO 4. NBS DMSO O°H Intermediate Product 3. Write the structure of the product from the first step (Product-1) and then the product from the second step (Product-2) for the two-step reaction sequence shown below. NABH, Hg(OAc), THF / H,O Product-1 Product-2