1. excess NH3 NH,CI NH2 OH + dry ether O Mgl H3C-Mgl CH4 a = Proton transfer e = Electrophilic addition h = Sy1 Nucleophilic substitution b = Lewis acid/base c = Radical chain substitution d = Radical chain addition i = Sy2 Nucleophilic substitution j = Electrophilic aromatic substitution f=E1 Elimination g = E2 Elimination Identify the mechanism by which each of the reactions above proceeds from among the mechanisms listed. Use the letters a - j for your answers.

1

O Complete the following chemical reaction catalyst b| H3C w CHz t HzO ) HgC a CHs + He Pd/Cy H3C ~CH3 t Br-Br e) ce 8 Chlorination of ethane under ultraviolet light 9 hydlogenation of buta-lyne with a phtinum catalyst.

Synthesize the following compound using only benzene and 3-hexyne as sources for carbon

Ph- OC XT :OH₂ Primary amines add to aldehydes and ketones to give imines. Imines are formed in a reversible, acid-catalyzed process that begins with nucleophilic addition of the primary amine to the carbonyl group, followed by transfer of the proton to yield a neutral carbinolamine. Protonation of the hydroxyl group converts it into a good leaving group and an E1-like loss of water yields an iminium ion. Deprotonation yields the product imine and regenerates the acid catalyst. Draw curved arrows to show the movement of electrons in this step of the mechanism. Arrow-pushing Instructions NHOH CH3 CH3 NH₂OH OH HN I Ph CH3 OH H₂O CH3 за

Saved For the following reaction, use the identity of the alkyl halide and nucleophile to determine which substitution mechanism occurs. Then determine which solvent affords the faster reaction CH;OH CH;OH HCI OCH3 or DMSO Multiple Choice O SN1. CH3OH O SN1, DMSO SN2 CH3OH O SN2, DMSO

Which of the following reagents is best to achieve the given transformation? H₂C 0=s=0 0000 → KOtBu OCH3OH NaOH TsCI, Py

Give the mechanism of the reaction shown below. CH3 H I С-СН3 I Br СН3 -с-с- I H E₁ нго

Which alkyl halide below is most likely to undergo a hydride shift in an S№1 substitution reaction? Br 66x6 Br B C Br XO B - D Br

Diazomethane can be used to convert a carboxylic acid to a methyl ester. Propose a mechanism for this reaction.