For each of the substrates below, identify whether: (A) the rate of substitution doesn't depend on nucleophile concentration and (B) the product distribution from substitution gives a 50/50 mix of enantiomers. If you answered "yes" for the first susbtrate, draw the intermediate that forms during a nucleophilic substitution reaction in the space below the table. Substrate Are both A and B true? Br. P Oyes Ono Oyes Ono Oyes Ono CI Oyes Ono X olo Ar

Draw a structural formula for the major organic product of each reaction and specify the most likely mechanism by which each is formed. (g) CH3CH2ONa++CH2=CHCH2Clethanol

The formation of Br2 from NBS first involves the reaction of NBS with HBr to form an iminol intermediate and molecular bromine. The intermediate then undergoes acid-catalyzed tautomerism to form succinimide, the byproduct of the reaction. Propose a curved-arrow mechanism for the conversion of NBS into succinimide that also accounts for the formation of Br2.

When performing a nucleophilic substitution reaction and not knowing the structure of the starting material or product, how can you form a method to determine whether the reaction proceeds via an SN1 or SN2 mechanism?

Like acid chlorides, acid anhydrides react with alcohols in the presence of pyridine to form esters. For the following reaction : (a) Draw a circle around the nucleophile ; (b) Draw a square around the electrophile; (c) Put a star next to the base; (d) Draw the structure of the tetrahedral intermediate in the box below. Then draw a reasonable 3-step arrow pushing mechanism for the reaction.

Using the pKa values of the conjugate acids of the leaving groups (the pKa of HBr is -9, and the pKa of H2O is 15.7), explain the difference in reactivity between CH3Br and CH3OH in a nucleophilic substitution reaction.

For the reactions below predict the product that will form via the stated mechanism then explain why using the stated effect the reaction will proceed through the supplied mechanism

The following substances can be prepared by a nucleophilic addition reaction between an aldehyde or ketoneand a nucleophile. Identify the reactants from which they were prepared. If the substance is an acetal, identifythe carbonyl compound and the alcohol; if it is an imine or enamine, identify the carbonyl compound and theamine. You do not have to consider stereochemistry. In cases where there is more than one answer, just giveone. Use Grignard reagents when an organometallic reagent is required. Draw the Grignard reagent as acovalent magnesium bromide.

a) Propose a stepwise synthesis for the compound below starting from benzene. List all reagents and intermediates. You can assume that ortho- and para- substituted benzenes can be separated efficiently. (3 reactions) Br O₂N b) Leveraging your knowledge of electrophilic aromatic substitution mechanisms, propose an arrow-pushing mechanism for the nitration step of the synthesis in a). Make sure to include all charges, intermediates, and the formation of the electrophile in this reaction. You can use benzene as a model reagent (see below). HNO3 H2SO4 NO2 c) Substituted benzyl halides can react with methanol via an SN1 mechanism to form benzyl ethers. List the benzyl halides below in order of increasing reactivity under these conditions (i.e., from the least reactive to the most reactive). Br II Br III Br IV Br

An organic chemistry experiment involves a nucleophilic substitution (SN2) reaction using 1-iodobutane and 2-naphthoxide ion. The 2-naphthoxide ion is generated from 2-naphthol and sodium hydroxide in an ethanol solvent. The experiment includes steps like generating the nucleophile, conducting the SN2 reaction, and analyzing the product using 1H NMR spectroscopy. Question: Write the structure of the undesired side product if CH3CH2O‾ (ethoxide) reacts with 1-iodobutane.