In the substitution reactions below, draw the major product in the box provided and indicate in...
Question 2. (20 marks) In the reactions below, draw the MAJOR product in the box provided and indicate in the small box whether the reaction is Sn1, S2, E1 or E2. Be sure to show all necessary stereochemistry. If more than one enantiomer is produced, write "+En" in the box with the product. Product Sy1/S2/E1/E2 H2SO4 Heat OH HC (44) OH NaOH NaCN DMSO, Cold NaOtBu Page 3 of 11
Key Topics: Nucleophilic Substitution Reactions (SNI or SN2. Reactions using PBr3. SOCI, or TCI. In the empty boxes, draw the structure of the MAJOR organic product expected following each reaction shown. If the reaction involves an SN2 reaction (or involves an SN2 step in the overall mechanism) clearly show the correct stereochemistry that will be observed in the product. Two of the reactions will involve a carbocation rearrangement. (4pts for each correct Major product drawn) H*, MeOH HO NaOH NaCN...
3. For each reaction, draw the structure of the major product(s) including stereochemistry where appropriate. Fill n the box below each arrow with the mechanism(s) that will be followed (SN1/E1, SN2, or E2). For SN1/E1 reactions, draw products for both. NaCN DMF tBuOH 言言言 MeOH * | CH30 CH OH DMSO R-2-bromopentane
17. Draw the structure of the major organic product(s) for each of the following reactions. Indicate stereochemistry when appropriate. C(CH3)3 NASH Br (S)-2-bromononane - acetonitrile KOH CH,OH NaCN HE Br Acetonitrile C2H5 H, Br NaOH Acetone excess HBr ROOR HC1 + Br Na o DMSO
1. Predict the major substitution product(s) for the following reactions. Include stereochemistry if appropriate. You may assume an aqueous workup is performed after each reaction. 1. Nah, DMF ТОН 2. Mel BrMg-Ph KCN 16 { ad ton ot MeOH HD Na Br Me DMSO EtOH Br ~ Br DMSO * Me OH LNH2 M HO Me-S (1 equiv) Me DMF
16. Give the major product that you would expect to be formed in each of the following reactions. If you think there is no reaction write NR after the arrow. In each case give the mechanism (SN1, SN2, E1 or E2) by which the product is formed. Also indicate the correct stereochemistry when applicable. Both product and the mechanism should be correct to get credit. No partial credit. Nal -BuOK Acetone t-Buo NaSH DMF Br, H NaOMe DMSO MeOH,rt t-BuOH...
3. Provide the product/s for the following reactions. Indicate if the reactions proceed via an SN1, or SN2 mechanism. Indicate proper stereochemistry if it is applicable. Show the mechanisms a h a NaCN DMF come NaSH DMSO NaOH DMSO a) M y NaOCHZ Naoch,, H2O NaOCH; HO
3. Shown below are a series of reactions. Predict the major product for each of them. Remember, you will need to first decide whether the reaction occurs by an SN2, SN1, E2, or E1 before you can determine what the product will be. Label each as SN2, SN1, E2, or E1. Hint: First decide whether S2/E2 or S1/E1 is favored, and then decide whether the reaction pathway goes by a substitution or elimination reaction. SN2 / SN1 E2/E1 Na DMSO,rt...
6) Predict the major product in each of the following reactions and indicate if it came from an Sn1, S2, E1, or E2 reaction. H3C Br NaOme CH3 H2O H Br MeOH 'BUOK H Br DMSO H3C Br NaOme CH3 H20 MeOH H OTS ЕКОН
1. For the following Alkyl halide indicate which position will react under SN1 reaction conditions and under SN2 reaction conditions. Explain your answer. mer 2. Draw the complete mechanism and the products for of the following SN1 reaction paying close attention to stereochemistry. H3C CI CH OH CH2CH3 општироотип солио 3. Provide the product/s for the following reactions. Indicate if the reactions proceed via an SN1, or SN2 mechanism. Indicate proper stereochemistry if it is applicable. Show the mechanisms NaCN...