1. For each of the following pairs of SN2 reactions, indicate which reaction occurs faster: a) CH:CH2Br + H20 OR CH2CH2BR + OH b) Remember the following is under an Sw2 condition: CH,CH2CHBr OH CH, CHCH,Br ČH3 OH OR
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- Organic Chemistry: Alkyl halides only 1. For each of the following pairs of Sy2 reactions, indicate which reaction occurs faster: a) CH;CH,Br + H0 OR CH,CH,Br + OH b) Remember the following is under an S2 condition: CH,CHCH,Br CH3 + OH CH;CH2CHBR + OH OR ČH3 2. What is the product of the reaction of ethyl bromide with each of the following nucleophiles? a) CH,CH,CH,0 b) CH,C=C c) (CH,)N 3. Arrange the following alky halides in order of decreasing reactivity in an Sy1 reaction: a) 2-bromopentane, 2-chloropentane, 1-chloropentane, 3-bromo-3-methylpentanemethanol + CH3OH Suppose you were told that the above reaction was a substitution reaction but you were not told the mechanism. Evaluate the following categories to determine the reaction mechanism and then draw the structure of the major organic product. Type of alkyl halide: Type of nucleophile: Solvent: Is the product racemic?Give the structures of the free-radical intermediates in the peroxide-initiated reaction of HBr with the following alkene. Include all lone-pair electrons and unpaired electrons. Hint: the radicals do not coexist in the same mechanistic step. сCH2 Hint: One organic radical and one inorganic radical.
- CH3 CH3 Br- Br2 CH2CI2 CH3 CH3 H3C H3C Br Electrophilic addition of bromine, Br2, to alkenes yields a 1,2-dibromoalkane. The reaction proceeds through a cyclic intermediate known as a bromonium ion. The reaction occurs in an anhydrous solvent such as CH2C12. In the second step of the reaction, bromide is the nucleophile and attacks at one of the carbons of the bromonium ion to yield the product. Due to steric clashes, the bromide ion always attacks the carbon from the opposite face of the bromonium ion so that a product with anti stereochemistry is formed. Draw curved arrows to show the movement of electrons in this step of the mechanism. Arrow-pushing Instructions CH3 CH3 Br- .CH3 .CH3 H3C H3C :Br :Br:Alcohols 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.9) Suppose I want to perform a simple substitution reaction, replacing the OH with a Cl in the following compound. Which of the following reagents works best? Explain (and that means explain why the wrong answers are wrong as well as why the right answer is right). Option A: Addition of HBr Option B: Addition of SOC12/pyridine Option C: Addition of SOCl2 only OH ? J1
- Predict the product and draw the mechanism of its formation. Include lone pairs and charges in your answer. Using wedges and dashes to indicate the stereochemistry as necessary. Do not use abbreviations such as Me or Ph in your drawings. Do not explicitly draw any hydrogen atoms in any of your products. & Me 13.16d1 1) LIAIH. 2) H₂O Draw the first step of the mechanism (Use H as the nucleophile). CH, +H Edit Drawing3. The following three SNAR transformations follow different mechanisms. Draw an intermediate or transition state for each reaction that relates the correct mechanism. Write a short sentence as to why that is the correct intermediate for the reaction. Reaction 1: Reaction 2: NO2 NO2 NO₂ + NaOMe NO2 + NaOH2 1. aq NaHCO3. 100 C 2. H₂O+ OMe NO2 NO₂ OH ŇO₂ NO2 Reaction 3: CFa Br CF3 8--2 + NaNH2 NH3 NH₂ Intermediate/transition state Intermediate/transition state Intermediate/transition stateDraw the major organic product of the reaction shown below. OH lan 8 [References] K₂Cr₂O7 H₂SO4, H₂O You do not have to consider stereochemistry. • You do not have to explicitly draw H atoms. In cases where there is more than one answer, just draw one. SALL ? ChomDoodlo ?
- 3. Assuming that the following reaction occurs under SN1 /E1 conditions, draw the structures of the products (there will be more than one isomer formed in each case) Page 15 of 16 CHEMISTRY 2400 EXPERIMENT 8: PRIMARY HALOALKANE: NUCLEOPHILIC SUBSTITUTION WINTER 2022 Substitution product(s) Но HBr HBr 15 Elimination product(s)7. Which one of the following alkyl halides would react faster by bimolecular nucleophilic substitution (SN2)? CH;CHa CH2= CHC chlorocydohexane (CHo)2CHCI Ph:Ca A В EDraw the major organic product of the reaction shown below. + PBr3 OH • You do not have to consider stereochemistry. • You do not have to explicitly draw H atoms. A