13. Predict the products for the following reactions. While the second reaction is a bit different, it is mechanistically identical the first. The nitrogen has a lone pair (like the oxygen) which adds to the boromonium ion as a nucleophile. A proton is then lost from the nitrogen to give the neutral reaction product. Br-Br OH Br-Br NH2
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- Which of the following molecules is most nucleophilic? OA. NaOCH₂CH3 OB. CH3CH₂OH OC. NaOC6H5 OD. C₂H5OH 1 E.CH3COONaVII. Predict the product(s) of the following cleavage reactions. HI H₂O 1. HI 2. H₂O x 3. HI H₂O9. Rank the following nucleophiles, in a solution of DMF, in order of weakest to strongest. НО CI Strong Br Slow II II IV
- In hydrobromination of 3-hexene, which of the following pairs of species act as nucleophiles? 3-hexene, Br– 3-hexene, HBr HBr, Br– HBr, Br2Predict 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 DrawingN3 H Predict the product of the following multi-step reactions. The points per question is the Number of Steps + 1 (2 steps = Show the intermediate of each step for partial credit considerations. NaH, then Br 1) Ph3P, H₂O 2) CH3l (3 eq), then Ag₂O 1) NaOH, 12 2) NaNH2( 3 eq)
- 7. Give a complete mechanism for the reactions below. NH =0 HCI Intermediate product 1. Mel 2. NaOH Final ProductFor each pair below, predict which member will be the better nucleophile stating your reasons why. a. NH3 vs H₂O b. CH3O vs OH- c. CH3O vs CH3OHThe alkyl halide shown reacts with sodium methoxide to form an organic product. H3C Br NaOMe H3C. HX CH3 H major organic product C H₂ CH3 Determine whether this reaction proceeds by SN1, SN2, E1 or E2 and identify the major organic product. Step 4: The protons in the alkyl halide are numbered. Identify the protons that will be abstracted by a strong base in an elimination reaction. 6 H3C Br CH3 H3C 1 5 The major product is formed from elimination of which proton(s)? 01 2 3 4 5 6 QIN CH+ H₂ CH3 3 Identify the ß-hydrogens 1 2 3 5 6
- 10. Alkyl diazonium salts decompose to form carbocations, which go on to form products of substitution, elimination, and (sometimes) rearrangement. Keeping this in mind, draw a stepwise mechanism that forms all of the following products. NaNO2 HO + `NH2 HCI, H2O HO,H Br Br2 CH2Cl2 H, Br Electrophilic addition of bromine, Brɔ, 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 CH2Clɔ. 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 H Br H- Br H. :Br: Proviouc NoxtWhich reaction schemes is best to give the product? ОН NO2 O The following reaction scheme: CH3 KMNO4 HNO3 Reaction intermediate Product КОН H,SO, H20 O The following reaction scheme: Br2 MeMgBr Reaction intermediate Product AIBR3 THE NO2 O The following reaction scheme: CH3 HNO3 KMNO4 Reaction intermediate Product H2SO4 КОН H2O