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Chapter 8 Practice problems PDF

Chapter 8 Practice problems PDF - l Chapter 8 Hyd xy...

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Unformatted text preview: l Chapter 8: Hyd xy Functional Group - Alcohols Discussion Sec on Problems 1. Draw the structs res of the following compounds: Triphenyl ethanol 9. 4-i 3-(brom methyll-4-octanol 3-cyclo nten-l-ol i. 3-cycloh xylpentan-3-ol j. Mesa-2, pentanediol k. 3-m thylhex-4-yne-2-ol Cyclope tene glycol ”99999 2. Predict which 'ember of each pair has the higher boiling point a d explain reasonJ for your predictions. a. l-hexan 'l or 3.3-dimethyI-l-butanol b. 2-hexan3ne or 2-hexanol c. 2-hexan " or 1,5-hexanediol d. 2-penta l or 2-hexanol 3. Predict which mber of each pair is more acidic and explain th reasons for your predictions. a. Cyclope 'tanol or 3-chlorophenol b. Cyclohe nol or 2—chlorocyclohexanol c. Cyclohe nol or cyclohexanecarboxylic acid d. 2,2-dichl ro-l-butanol or t - butanol 4. Show how you ould synthesize the following alcohols from appro 'ate alkenes. 5. Draw the organ? products you would expect to isolate from the f llowing reactions (after hydrolysis) i (j to“: + Nana. DHstOM), H,O 2)NaBH‘ (o) (CH;=CH)2 + cascuzcuacacuzg, 6. Show how you ould accomplish the following transformations. (I) —’ H OH ‘0) Ph—Clizmga —' Ph—CH2CH2CH;OH 7. CHALLENGE: ge inal diols or I, i-diols. are usually unstable spont neously losing water to give carbonyl compounds. Therefore, germinal dials are regarded as h drated forms of ketones and aldehydes. ropose a mechanism for the acid catalyzed loss f water from propane-2, 2- diol to give ace ne. H + O 4 X +69 Pmre_2' 27C“ OCCTDfle 8. CHALLENGE: gnord reagents react slowly with oxetane to pr ce primary alcohols. Propose a mec nism for this reaction and suggest why oxetane eocts with Grignqrd reagents even ough most ether: do not. ...
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