79 3. Complete the following reaction and write a mechanism for both the substitution and elimination products (both substitution and elimination products occur simultaneously). Discuss all criteria including stereochemistry when a chiral secondary primary alkyl halide with (S) configuration reacts with methanol a weak nucleophile. Draw energy profile for this reaction. (4 points) CH2CH3 CH₂O-Na+ + Br H3C (S) no 1999b 02.907 90 +20110
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- Draw a structural formula for the major organic product of the following reaction: CH2CI2 Br2 CH3CH=CHCH2CH(CH3)2 + Show product stereochemistry IF the reactant alkene has both carbons of the double bond within a ring. • Do not show stereochemistry in other cases. • If enantiomers are formed, just draw one. opy aste - [F ChemDoodleDraw the structure for an alkene that gives the following reaction product. CH212, Zn/Cu Ignore alkene stereochemistry. • You do not have to explicitly draw H atoms. In cases where there is more than one answer, just draw one. C P opy aste ChemDoodle®1) Predict the major products or substrates of the following reactions. If it is possible, write all stereoisomers. (10p) 1)Hg(OAc)2, THF, H20 (1) NaNH2 2) NaBH4, ОН (2)BzBr (3) H2/Li, ETNH2 b) HCI e) 1) O3 no peroxides 2) Zn/ACOH (1)OsO4 (2) NaHSO3, H20
- 46. Rank these compounds from least to most reactive towards nucleophilic aromatic substitution. CH CI NO2 O,N NO2 NO2 O,N NO2 III II (A) IIIPara-substituted product was produced when phenol reacts with cyclohexanecarbonyl bromide in the presence of AIB13. -Br Cyclohexanecarbonyl bromide (i) Outline the mechanism for this reaction. (ii) Draw the alternative substituted product formed.Identify the major organic product(s) generated from the reaction shown. CH3 "D + enantiomer 1 OI D₂ Pd/C DO CH3 "D + enantiomer 11 CH3 + enantiomer ||| CH3 P.H "D + enantiomer IV(a) Rank the following carbocations in order of increasing electrophilicity (1 = lowest electrophilicity, 4 = highest electrophilicity). (b) Rank the following 1,1-halomethylcyclopentanes in order of reactivity in an SN1 reaction (1 = lowest reactivity, 4 = highest reactivity. CH3 CI B with SNI, nor reactive means more stable (c) Rank the following species in terms of increasing nucleophilicity in an SN2 reaction in a po aprotic solvent (1 = lowest nucleophilicity, 4 = highest nucleophilicity).11. Which alkynes will give a single product when treated with Sin BH followed by H₂O, and aqueous NaOH? CH₂ (A) II and III (C) I and II 12. What is the IUPAC name of this compound Energy-> 11 13. Which statement is TRUE for this reaction coordinate diagram? 111 (B) I and III (D) I, II, and III (A) (2)-oct-5-en-2-ync (B) (E)-hept-5-en-2-yne (C) (E)-oct-3-en-6-yne (D) (E)-oct-5-en-2-yne Sia:BH IV 8- 111 VII Reaction Coordinate (A) The conversion of I to VII is endergonic, (B) There are five intermediates in this reaction. (C) The conversion of III to V is the rate-determining step. (D) There are four steps in the reaction mechanism. ACE ACS ACSAlcohols are important for organic synthesis, especially in situations involving alkenes. The alcohol might be the desired product, or the OH group might be transformed into another functional group via halogenation, oxidation, or perhaps conversion to a sulfonic ester derivative. Formation of an alcohol from an alkene is particularly powerful because conditions can be chosen to produce either the Markovnikov or non-Markovnikov product from an unsymmetrical alkene. Using your reaction roadmap as a guide, show how to convert 4-methyl-1-pentene into 5-methylhexanenitrile. You must use 4-methyl-1-pentene and sodium cyanide as the source of all carbon atoms in the target molecule. Show all reagents needed and all molecules synthesized along the way.(4)Rank the following compounds in order of reactivity toward an SÂl reaction. (1-best) CH3CH₂Br H₂C=CHC(Br)CH3 H₂C=CHBr CH3CH(Br)CH3The reaction below is the addition of HCl to 3-methylenecyclohex-1-ene. CH2 + HCI (i) Draw and name the kinetic and thermodynamic products structures of this reaction. (ii) Show the mechanism of reaction, while explaining the kinetic and thermodynamic preference of the reaction.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.SEE MORE QUESTIONS