In each reaction below: CH3-CH-CH3 + Cl CH3-CH=CH₂ + H-Cl :C1: CH3-CH-CH3 H CH3-CH-CH₂ + 7a. Label the nucleophile (Nu) and the electrophile (E). 7b. Draw arrows on the structures showing electron flow in the reaction.
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- Consider the following pair of nucleophiles in DMSO. Which is the better nucleophile: a: CN or b: F ? Answer by typing a or b. Better nucleophile = Consider the following pair of nucleophiles in CH3 OH, Which is the better nucleophile: a: N3 or b: CH3 COO ? Answer by typing a or b. Better nucleophile =Draw the most stable resonance form for the intermediate in the following electrophilic substitution reaction. OH CH3 + + H3C CH₂ CH3 First stage in synthesis of the preservative BHT • You do not have consider stereochemistry. • Include all valence lone pairs in your answer. • In cases where there is more than one answer, just draw one. ▼ H3PO4 ? OH CH3 CH3 CH3 CH3a. Identify two alkenes that react with HBr to form 1-bromo-1-methylcyclohexane without undergoing a carbocation rearrangement. b. Would both alkenes form the same alkyl halide if DBr were used instead of HBr? (D is an isotope of H, so D+ reacts like H+.)
- 4. What are the products obtained from the following elimination reaction? Indicate the major product. CH3 CH,CH,ČCH, H2O 5. a) Determine the major product that is formed when the alkyl halide reacts with a hydroxide ion in an elimination reaction. CH;CH,CH,CH,CCH, Br b) For the major elimination product obtained in 5a), which stereoisomer (cis or trans) is obtained in greater yield? Draw the two isomers and provide the names of the compounds.II. Apply all the criteria for each reaction, and then draw the product(s) of each. a) b) 9 d) Br X² CH3CH₂O CH3 Br CH3 CH3 Br + j EtOH CH3CH₂CI CH3OH heat ? CH3ONa CH3OH ? ? i ? 19. 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 tbe
- 10. A compound X of molecular formula C8H12 with no triple bonds reacts with one equivalent of H2 to give a new compound having molecular formula CaH14. What can be inferred about the structure of compound X? A) Compound X has 3 rings. B) Compound X has 3 pi bonds. Compound X has 1 ring and 2 pi bonds. D) Compound X has 2 rings and 1 pi bond. 11. Determine the product of the following reaction. H, Lindlar's cat. %3D IV A)I B) II C) III D) IV Type here to search 互i | A C 三DName each alkene and specify its configuration by the E,Z system. Cl- Cl I a. b. Br С.1% mol Pd(OAc)2 4% mol Ph3P B с CH3CN A (1 ring) (2 rings) (3 rings) The above reaction involves two sequential Heck reactions and three organopalladium intermediates. In the box below draw the structure of intermediate C. • You do not have to consider stereochemistry. • You do not have to explicitly draw H atoms. • Do not include lone pairs in your answer. They will not be considered in the grading. • Use R1 for the PdL₂I group. The R group tool is located in the charges and lone pairs drop-down menu. Sn [F ?
- 7. a) A) In the box below the arrow, label if the pericyclic reaction is a Diels Alder (DA), Electrocyclic (EC) or Sigmatropic Rearrangement (SR). B) Determine the major product(s). heat HO₂C b) heat to c) + 1. Na, NH3 NO2 NO2 2. heatH₂C- 6 -CH₂ Gently warmed H₂Cl H H₂C- 65 CH₂ -CH₂ 5 H₂C CH₂ 1a) Is the diene in the correct s-cis orientation to react? 1b) Would you describe the dienophile as having the ketone groups cis or trans? 1c) When you start with this cis-dienophile, what orientation must the ketone branches have to one another in the product? 1d) In this product, the dienophile approached from below pushing the 1 C bridge upwards. Which carbon of the product has an error as a result of the reaction's stereospecificity?Draw the most stable resonance form for the intermediate in the following electrophilic substitution reaction. CH3 CH3 H3PO4 HO, + H3C CH3 HO HO First stage in synthesis of the epoxy and polycarbonate ingredient bisphenol-A 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.