Question

5) (8 pts) Arrange the following compounds from most acidic through neutral to most basic. Briefly explain your reasoning. 7) (15 pts) a) Write out the 3-step arrow pushing mechanism showing how 1-pentene is hydrated to make 2-pentanol. b) Draw the other 2 alkenes (don't forgel cis/trans isomers!) that could also be hydrated to make 2-pentanol. Briefly explain why 1-pentene is the best choice. II, II,O a) heat Acidic Neutral Basic 6) (18 pts) Consider the Fischer projections of the following pair of stereoisomers. Name each structure in the pair according to IUPAC nomenclature, using appropriate R/S designation lo show handedness. CH3 CH3 H+Br Br H+OHHO+H CH,CH, CH.CH Draw the missing stereoisomers in this set. Indicate the relationship (enantiomers or diastereomers) between every possible pairing of compounds. Circle a pair of compounds that, if present in cqual amounts, will not show optical activity. If one of these compounds has a specific rotation of +4.29 when isolated, what is the specific rotation of the other?

Answer 1

nature can be explained on the dic & Basie following base Ald: donate it easily Base : donate lone lone pair pair through through species eletronega eletronegative les. No ) aud (b) o NH 2 : base 1 lip by N) (H+) thom : acid (H) (d) Ócom : acid (HT) base C (f) Agneth : base Up by ) (lp by N) : neutral no donation) on the basis of order of acid ease of (HP & lone pair) donating herrel rebare will be as 1° По )na fron a ohon < Dom moat acidic on "ment hormd Quid weak du to neighausing Flelectronegative) alia neutral < br < oricorum as tertiary primary looy weak base Ň will be in conjugation amine anne so writing the order in alphabelo (c) < (a) < (d) < (9) < (f) < ces < (6)

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