Consider this step in a radical reaction: CH3 Br What type of step is this? Check all that apply. Draw the products of the step on the right-hand side of the drawing area below. If more than one set of products is possible, draw any set. ооооо substitution propagation electrophilic termination none of the above X
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- PART 2 - Resonance 1. Construct a reaction diagram including 2-methylpenta-1,3-diene and H- Br as the reactants. Include all lone pairs of electrons. 2. Identify the nucleophile and the electrophile in the drawing above. 3. Draw a double headed arrow beginning at the nucleophilic pi electrons of the double bond in the 3 position of 2-methylpenta-1,3-diene and ending on the electrophilic hydrogen. Make sure to push the electrons in the bond between the H and Br onto the Br, with a double headed arrow, so that the octet rule (actually the duet rule for H) is obeyed. 4. Draw all of the possible intermediate(s) that can result from this attack. Try to draw these with the correct bond angles and shapes. 5. Identify the one that is most stable by circling it. 6. Using a double headed arrow show the nucleophilic electrons on Br attacking the most stable intermediate drawn above. 7. Draw the product(s) that is/are formed. Include any stereochemistry involved. 8. Name the product(s). 9. Repeat…4. Determine the products of each of the reaction steps shown by curved arrow notation. Label the nucleophile and electrophile. CH, CH, a. CH,CH,-Br: c. CH,C=CCH, H-Ci: b. CH 1 CH, Hộ: -:NH,Construct a three-step synthesis of 1-bromopropane from propane by dragging the appropriate formulas into the bins. Note that each bin willl hold only one item, and not all of the given reagents or structures will be used. Reactant Reagent 1 Step 1 Product Reagent 2 Step 2 Product Reagent 3 Final Product (1-bromopropane) (propane) Br2 Br2 (CH)3CO K HBr ROOR HBr NBS ROOR HaC Нас Нас, Нас Нас НаС. hv CH2 CH2 CH Нс CH-Br CH-Br CH Нас Нас, нC Нас НаС Br Br Br
- 17. a. Label the reactive features, highlight the most reactive one, then highlight what it needs. Also, state if the reaction will start to create a carbocation, carbon radical, or carbanion, or will cause loss of aromatic character. If a carbocation, carbon radical, or carbanion starts to develop, label where that will occur. CH3 with Cl, and FeCl, CH2 CH3 b. Use mechanism arrows to illustrate the reaction that occurs. c. If applicable, use stabilization resources to deal with the carbocation, carbon radical, or carbanion that starts to develop during the reaction, and draw the structure of any resonance-stabilized intermediate. d. Continue labeling and diagramming the reaction until you find the major stable product(s). e. Finally, state the stereochemistry of the major product(s) and use either Fisher projection or perspective formula representations to illustrate that stereochemistry.17. a. Label the reactive features, highlight the most reactive one, then highlight what it needs. Also, state if the reaction will start to create a carbocation, carbon radical, or carbanion, or will cause loss of aromatic character. If a carbocation, carbon radical, or carbanion starts to develop, label where that will occur. -CH3 with H,SO, b. Use mechanism arrows to illustrate the reaction that occurs. c. If applicable, use stabilization resources to deal with the carbocation, carbon radical, or carbanion that starts to develop during the reaction, and draw the structure of any resonance-stabilized intermediate. d. Continue labeling and diagramming the reaction until you find the major stable product(s). e. Finally, state the stereochemistry of the major product(s) and use either Fisher projection or perspective formula representations to illustrate that stereochemistry.4. Circle the electrophilic and nucleophilic atoms in each substitution reaction below. Provide the neutral organic product; where a stereocenter is created, use a wavy bond to indicate a mixture of configurations or wedges/dashes for stereospecific reactions. Also, provide the dominant reaction mechanism (Sn2 or SN1) somewhere in each box. A. Br NaSEt DMF В. ELOH C. .SO2NHNA Cl + D. NaH Br- HO, DMF
- Macmillan Learning Use the table of bond dissociation energies to calculate and compare the enthalpy of monobromination and monochlorination for the given alkyl position. Bond Dissociation Energies (for A-B- A+B) Bond broken H-H Br-Br CI-CI CH₂CH₂CH₂-H+ Br₂ CH₂CH₂CH₂-H + Cl₂ AH (kJ/mol) Bond broken AH (kJ/mol) 436 366 193 432 243 H-Br H-Cl CH₂CH₂CH₂-Br + HBr CH₂CH₂CH₂-CI+HCI Bond broken AH (kJ/mol) CH₂CH₂CH₂-H 423 CH₂CH₂CH₂-Br 294 CH₂CH₂CH₂-CI 354 AH = ΔΗ = -58 Incorrect -131 Incorrect kJ/mol kJ/molShow how you might synthesize this compound from an alkyl bromide and a nucleophile in an S№2 reaction. N3 • Use the wedge/hash bond tools to indicate stereochemistry where it exists. • Only draw the reactants. Separate multiple reactants using the + sign from the drop-down menu. • If there is more than one possible combination of alkyl bromide and nucleophile, draw only one combination. • Do not include counter-ions, e.g., Na+, I, in your answer. 90-85 TAYY ? ChemDoodle O OO. #[ ] درDraw one product of an elimination reaction between the molecules below. Note: There may be several correct answers. You only need to draw one of them. You do not need to draw any of the side products of the reaction. HO + + X S & Click and drag to start drawing a structure.
- Part 1. Radical Reactions. Consider the following reaction. H + Bro + HBr AHrxn= (+) a) Assume the reaction above is endothermic and draw the transition state. (Be sure to include the relative bond lengths). b) Redraw the starting materials below and provide a reasonable mechanism for the products formed. Be sure to use curved arrows to show the pushing of electrons.Q3. For the substitution reactions below, draw out the reactions as shown and answer the following questions for each example: (i) Draw the structure of the unknown product(s) of the reaction. (ii) Identify the nucleophile, electrophile and the leaving group for each step. (iii) Identify each mechanism as Sn1 or Sn2. (iv) Insert curly arrows to represent the reaction mechanism. b. Br NH3 Product C Product DFor the reduction of 2-methyl cyclohexanone to methyl cyclohexanol using NaBH4... 1. What is the reaction mechanism (draw curved arrows)? What is the nucleophile? Electrophile? 2. Using your reaction mechanism from the above question, sketch the reaction coordinatediagram. What does the transition state most likely look like? What is the rate-determining step?