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- Which of the following compounds is the most nucleophilic? . CHSSH • CH;OH H2O CH,CO2H BF3The behavior of esters and ketones in a reaction with a nucleophile is different because: 1) the carbonyl of the ketone is more positive. 2) the ester cannot form a tetrahedral intermediate. 3) the two oxygens of the ester sterically hinder the nucleophile attack. 4) there is a reasonable leaving group in the ester. O 2 O 4 O 1H 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 Noxt
- In the following reaction, the nucleophile is: CH₂CH₂Br 3-phenylpropanenitrile cyanide ion Water 1-ethylbenzene bromide e OH PCN H₂O Write the product of the reaction: H + H +O eq -I CH₂CH₂CNWhat is the nucleophile in the following reaction? 2H2 0 + CH3! → CH3OH +F + H3O* 12 O CH3I O CH3OH O H3O*Provide the correct sequence of the steps involved in the following reaction: H3C CH2 H3C Br2 HBr но Br Step 1 [Choose] Nucleophilic attack on Bromine Carbocation rearrangement Proton transfer to bromide ion Step 2 Nucleophilic attack by water Leaving group leaves Nucleophilic attack by hydroxide Step 3 Generation of bromonium ion Step 4 [ Choose ]
- In an SN2 reaction between 2-chlorobutane and iodide ion, what happens to the rate of the reaction if: (a) the concentration of 2-chlorobutane is doubled? (b) the concentration of iodide is doubled?methanol + 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?Consider the following SN1 reaction: (CH3)3CBR + H2O → (CH3)3COH + HBr What is the effect of doubling both the t-butyl bromide and water concentrations on the rate of the reaction? O doubles the rate O quadruples the rate O triples the rate O halves the rate O no change O quarters the rate O 1/16th the rate
- Assuming that the nitrogen in enamine is sp hybridized, explain why the double bond of an enamine is more nucleophilic than a typical alkene double bond. Propose the mechanism for the reaction below and use resonance structure to explain why the other regioisomer does not form. Br HBr OCH3 OCH3Identify the nucleophile in the following reaction. OOOO Br CH3CN O Nat Br HS Save for Later NaSH CH3CN SHIn the presence of a nucleophile, which of the following will most likely undergo conjugate addition? B) OCH3 A) D) O A ов C OD