Rimantadine was among the first antiviral drugs to be licensed in the United States to use against the influenza A virus and to treat established illnesses. It is synthesized from adamantane by the following sequence:
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What is the structure of nucleophile 3? Thank you.
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- Rimantadine was among the first antiviral drugs to be licensed in the United States to use against the influenza A virus and to treat established illnesses. It is synthesized from adamantane by the following sequence: CH₂=CHBr AlBr3 (2) Adamantane =D₂.-6. (3) -Br Br (4) Ø Br₂ (1) a Step 2 proceeds via the following mechanism: 1-bromoadamantane (5) Br SnF ChemDoodle Rimantadine 1. AlBr, acts as a Lewis acid to yield carbocation 1; 2. Bromoethene acts as a nucleophile to give carbocation 2; 3. Carbocation 2 reacts with nucleophile 3 to give the product of reaction 2. Work out this mechanism on a separate sheet of paper and then draw the structure of nucleophile 3. NH₂ ==starting points == ✔(b) Predict the suitable solvent (H2O or CH3COCH3) to increase the reaction of bromopropane (CH3CH2CH2B1) with sodium hydroxide (NaOH). Two reactions are shown below: NaOH, 55 °C CH;CH,CH,Br CH;CH,CH,OH + NaBr H,O (i) NaOH, 55 °C CH;CH,CH,Br CH;CH,CH,OH NaBr H,C CH (ii)CHE2613/101/0/2022 The reaction of methylpropene with HBr, under radical conditions, gives two 3.2 intermediates. Propose a mechanism for the formation of the two products. (8) Propose a mechanism for the following reaction and use electronic factors to account for 3.3 the formation of a major product: CH2 CH2Br N-Bromosuccinímide (NBS) ho, CCI4 (2) 3.4 Draw the structure of an antioxidant, Vitamin E free radical and use resonance structures to account for its stability. (9) Question 4 [38] 4.1 Use electronic factors to explain why methyl carbanion is more stable than tertiary butyl carbanion. (9) 4.2 Rank the following intermediates in order of increasing stability. Account for your choice: :CH2 :CH2 CH2-CH2 :CH2 NO2 CH3 OCH3 (8)
- n-Pentanol (CH3CH2CH2CH2CH2OH) and 2-methylbutan-2-ol (CH3CH2C(CH3)2OH) are converted to their corresponding alkyl chorides on being reacted with hydrogen chloride. (a) Write out an equation for each reaction (b) Assign each the appropriate symbol (SN1 or SN2) (c) Write a suitable mechanism for each reactionA medicinal chemist at Orgalex Labs, a little known division of a big international pharmaceutical firm, has predicted the major product of the following reacti an early step in the synthesis of Compound R40 (rumored to be a cure for rhinitis, spontaneous combustion, and bad luck): or=0x0 HBr OH As Vice-President of Research, it's your job to decide whether the chemist has made a reasonable prediction. • If your answer is yes, these could be the major products of the reaction, draw the complete mechanism for the reaction below. • If your answer is no, check the box under the drawing area. Ö U OH Br H-Br Add/Remove step Click and drag to start drawing a structure.1.The actual yield of Compound (4) is 1.0g. What is the Theoretical Yield and the Percent Yield of Compound (4)? rOCH CH3 OCH,CH3 Esterase OR OH ethyl 3-hydroxybenzoate (2) ethyl 3-acetoxybenzoate (3) 3-acetoxybenzoic acid (4)
- (b) Predict the suitable solvent (H2O or CH3COCH:) to increase the reaction of bromopropane (CH3CH2CH2B1) with sodium hydroxide (NaOH). Two reactions are shown below: NaOH, 55 °C CH;CH,CH,Br CH;CH,CH,OH + + NaBr H,O (i) NaOH, 55 °C CH;CH,CH,Br CH;CH,CH,OH + NaBr (ii) H,C- CH3Organotin compounds play a significant role in diverse industrial applications. They have been used as plastic stabilizers and as pesticides or fungicides. One method used to prepare simple tetraalkylstannanes is the controlled direct reaction of liquid tin(IV) chloride with highly reactive trialkylaluminum compounds, such as liquid triethylaluminum (Al(CzHs)3). 3SnCl4 + 4Al(C2H5)3 → 3Sn(C2H5)4 + 4AlCl3 In one experiment, 0.160 L of SnCl4 (d= 2.226 g/mL) was treated with 0.346 L of triethylaluminum (Al(C2H5)3); d = 0.835 g/mL). What is the theoretical yield in this experiment (mass of tetraethylstannane, Sn(C2H5)4)? If 0.257L of tetraethylstannane (d= 1.187 g/mL) were actually isolated in this experiment, what was the percent yield?A student attempted to prepare 1-chlorobutane by mixing 1-butanol with NaCl in acetone. Was the student succesful? Explain.
- (c) The structures of lycopene, beta-carotene and retinol are shown below. Lycopene Beta-carotene H3C CH; CH3 CH3 OH Retinol (vitamin A) CH3 Using appropriate reaction mechanisms: (i) Show how lycopene is converted into beta-carotene. (ii) Briefly explain how retinol is formed from beta-carotene.1. The following synthetic schemes all have at least one flaw in them. What is wrong with each? (a) Br CO2H CH3CH2CHCH2CH3 1. Mg CH3CH2CHCH,CH3 2. NaCN 3. H30* (b) .CH2CO2H „CH2CH3 1. LIAIH 2. H30* (c) он он CH3CCH2CH2CI 1. 1. NaCN 2. H30* CH3CCH2CH2COH CH3 CH3Organotin compounds play a significant role in diverse industrial applications. They have been used as plastic stabilizers and as pesticides or fungicides.One method used to prepare simple tetraalkylstannanes is the controlled direct reaction of liquid tin(IV) chloride with highly reactive trialkylaluminum compounds, such as liquid triethylaluminum (Al(C2H5)3). 3SnCl4 + 4Al(C2H5)3 3Sn(C2H5)4 + 4AlCl3 In one experiment, 0.230 L of SnCl4 (d = 2.226 g/mL) was treated with 0.396 L of triethylaluminum (Al(C2H5)3); d = 0.835 g/mL). If 0.335 L of tetraethylstannane (d = 1.187 g/mL) were actually isolated in this experiment, what was the percent yield?