9. Provide the major dehydration product of the following reaction. Recall which of the four substitution and elimination reactions a dehydration is. Before you do your SN# or E# mechanism, remember what heteroatoms do in the presence of an acid (aka-the-OH is a bad leaving group, but protonating it might turn it into a good one). Don't forget to apply the concept from the previous question. OH #14 H+ A
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- 2. Draw the structures and explain why CH3CH₂O and CH3CO₂ are good nucleophiles but CH3SO3, water, and alcohols (R-OH) are poor nucleophiles. Propose a 'cutoff' for the amount of negative charge needed to be a good nucleophile. CH3CH₂O CH3CO₂ CH3SO3 H₂O CH₂OHb).. .. Under each potential product of this E2 elimination, write "major product," "minor product," or "not formed." Me Br H Me Me OH Me Ph Ph H Me H Et Me Me Me Ph Ph Me Me EtConstruct a three-step synthesis of trans-2-pentene from acetylene by dragging the appropriate formulas into the bins. Note that each bin will hold only one item, and not all of the given reagents or structures will be used. (Me methyl, CHs; Et ethyl, CH3CH2.) Reactant Product Reagent 1 Reagent 2 Step 1 Product Step 2 Product Reagent 3 (acetylene) (trans-2-pentene) Li HBr На Pt 1) NaNH2 2) Me н CH3CH2NH2 H H 1) NaNH2 2) EtBr
- Q10. For each of the following reactions (a-b), predict whether the substitution is more likely to occur following an Sn1 or Sn2 mechanism; explain your reasoning. Draw the products of each nucleophilic substitution paying particular attention to the stereochemistry of carbon 1. a) Br, CH3 MeOH H3C b) Br NaOH 1 DMF* H3C *N,N-dimethylformamideConstruct a three-step synthesis of 1-bromopropane from propane by dragging the appropriate formulas into the bins. Note that each bin willl hold only one item, and not all of the given reagents or structures will be used. Reactant Reagent 1 Step 1 Product Reagent 2 Step 2 Product Reagent 3 Final Product (1-bromopropane) (propane) Br2 Br2 (CH)3CO K HBr ROOR HBr NBS ROOR HaC Нас Нас, Нас Нас НаС. hv CH2 CH2 CH Нс CH-Br CH-Br CH Нас Нас, нC Нас НаС Br Br Br9) 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
- 3) Use the reaction shown below and the associated reaction energy diagram to answer the following questions. E A Но- + Br HO. Br- reaction coordinate a) In the space above, use curved arrows to show the mechanism of the reaction. b) Classify the reaction as either addition, elimination or substitution. c) In this reaction is hydroxide (HO-) acting as a nucleophile or as a base? c) Based on the reaction energy diagram, is the reaction endergonic or exergonic? d) Based on the reaction energy diagram, and assuming the reaction is reversible, would the equilibrium lie to the left or to the right? e) Which position on the reaction energy diagram (A, B or C) corresponds to the transition state?This reaction is an example of conjugate addition of a nucleophile to an a,ẞ-unsaturated carbonyl. O CH3CH2CH2CH=CHCSCOA H₂O OH CH3CH2CH2CHCH2CSCOA Draw the two resonance structures of the enolate anion intermediate for this reaction. • Draw an R1 group in place of COA. The R group tool is located in the charges and lone pairs drop-down menu. • Draw one structure per sketcher. Add additional sketchers using the drop-down menu in the bottom right corner. • Separate resonance structures using the symbol from the drop-down menu. ->> 90-87 O + ? ChemDoodle >Choose the reagent(s) that would be most likely to complete this reaction. I||| / A B C D 1. BH3-THF 2. H2O2, NaOH Br₂ H₂O OsO4 (catalytic) NMO RCO3H Done
- 5. Complete this sequence of reactions. Provide a mechanism for each step along the way. 1) CH₂MgBr 2) H₂O+ ? 1) NaH 2) CH₂CH₂BrDraw the major organic product of the Bronsted acid-base reaction. Include all lone pairs and charges as appropriate. Ignore any counterions. ] NaH OHDraw one product of an elimination reaction between the molecules below. Note: There may be several correct answers. You only need to draw one of them. You do not need to draw any of the side products of the reaction. HO + + X S & Click and drag to start drawing a structure.