10. Draw a line structure for each organic product of the reaction shown below, including relevant stereochemistry. Do not draw multiple structures of the same compound. (6 pts) SN2 + HBr ???? OH
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- (4)Rank the following compounds in order of reactivity toward an SÂl reaction. (1-best) CH3CH₂Br H₂C=CHC(Br)CH3 H₂C=CHBr CH3CH(Br)CH379 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 +2011010:26 None of the above 2 Arrange the following alkanes, in order of increasing the reactivity reaction toward halogens in presence of heat. CH, HC CH3 CH3 H,c CH, H-C CH3 1. TTT O I> I|> || Il>1> |II I> III > II Il >I> II| None of the above
- 7 2233 b) Br Br → 2 Br. Br. entt wollot Florition #live DOFDAY Wn't sonic. 6. (6 pts) Draw stepwise mechanisms for the reactions below. Use appropriate curved arrows to show all bonds broken and formed, and draw all intermediates with appropriate charges. (3 pts each) a) Br2 Draw initiation and both propagation steps: OH мон H₂SO4 heat → SAY hv + H₂SO4 HBr d. + H₂O + - Br 10. DOY + HBr Section + Br-Br→→ X Br No + HBr + Br Chemistry 88, No. 3 (2016) Esc Tab Cap Shif Ctrl7. Draw the major organic products obtained from the following reactions? (4pts) Br NaOCH2CH3 CH3CH2OH -CI NaOCH2CH3 CH3CH2OHGive the IUPAC name for the followving alcohol. Be sure to answer all parts. Но HO Η H. [Also label the stereogenic centers as R or S.] (2R.3R) (select) (seleet) H3 ol v
- ― 6 Give the organic product: A NO₂ -NH₂ & Sn. HCl(aq) dil NaOH(aq) NH heat B D OH ? -NO₂(6) SN2 Reactions: Nucleophiles. Rank the following nucleophiles relative to their SN2 reactivity toward 2- bromopropane (1=fast.4-slow). IN GENERAL, the stronger base = more reactive nucleophile. CHẠCH,OH CH;CH;O Na* Na* NH: NH33. Sketch a free energy diagram for the reaction of each alkyl radical shown below with -OH. Be sure that your diagram reflects the relative stability and persistence of each species given below. (3 marks) TH H BDE 75 kcal/mol BDE = 82 kcal/mol KOH = 1010 S-1 OH Тон KOH = 1011 S-1 'OH OH
- PQ-6. What is the rate determining step of this reaction? CH₂CH3 (A) HOTS H3C (C) NC CH₂CH3 HOTS H3C CH₂CH3 NaCN Hi H3C (S)-isomer (B) OTS acetone Hi H₂C (D) NC CH₂CH3 CO-H Ts CH₂CH3 ∙H H H₂C CO CN H H3C CH₂CH₂ (R)-isomer1 D D eq M eq [References] Draw a structural formula for the major organic product of the reaction shown below. &. (02)00 CH₂ CuLi CH3CH₂0 2 ether • You do not have to consider stereochemistry. + ? H30+34. Draw the major organic product(s) for the following reactions; (*) must include correct stereochemistry; double-dagger (+) must show two products. HBr (a)* Br HBr Br (b) + (1.00 equiv.) Br Br HBr (c)* HCI (d) 48% wt. HBr 37% wt. HCI HEAT OH [H2SO]/ H20 (g) OCH3 [H2SO,]/A CH,OH (excess) (h) [H,SO,1/H20 OH (i)* [H2SO,] / H,0 OH 13
