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practiceexam3key - 1 O O a b Br C OH c Br d C OH Cl...

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1. Name the following molecules using systematic naming. Br C OH O Br Cl C OH O Br OH OH Cl OH O O Cl O O N H O OH O OH Br Cl O Br O O O a) b) c) d) e) f) g) h) i) j) k) l) m) n) bromobenzene benzoic acid 1-bromo-4-chlorobenzene 3-bromobenzoic acid 2-methylbutan-1-ol 2-ethylcyclohexanol 4-chloro-3-ethylpentan-2-ol 2-methoxypropane 2- sec -butoxybutane ethyl 3-chloro-4-methylpentanoate N -isopropyl-2-methylbutanamide 5-bromo-2-hydroxyhexanoic acid 4-bromopentanoyl chloride butanoic anhydride isopropylmethyl ether or 2-methoxypropane 2. Show the expected products of substitution reactions for the following reactants. Indicate whether it would undergo an SN1 or SN2 reaction and WHY.
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H 3 C H 2 C Br OH + H 3 C H 2 C Br OH H 2 C H 3 C OH + Br ‐This reaction undergoes SN2 because the secondary carbon that needs to be attacked by the hydroxide would not make a stable carbocation intermediate so the halide needs to be pushed off by the attack of the nucleophile. Also, there is little
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