Name or draw as appropriate. IUPAC rules apply. N-ethyl-5-methylhexanamide 2. Circle the more acidic compound of each pair. Н. F ОН ОН ОН ОН ОН ОН ОН ОН F- MeO HO. HO. HO, ОН O2N 1.
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- 7. Draw the conjugate base for each. CH;CH2OH → CH:CH;CH3 → CH:CH2NH2 – CH:CH2SH –4- Circle the strongest base. a) CH3O 6 CH3NH2 b) Clo I c) CH3CO or CF3CO2НО. meta-Hydroxyacetophenone HO para-Hydroxyacetophenone The conjugate base of the para isomer has a negative charge that is delocalized over atom(s), and the conjugate base of the meta isomer has a negative charge that is delocalized over oxygen atom(s). Therefore, the conjugate base of the meta isomer is carbon atom(s) and isomer, making meta-hydroxyacetophenone oxygen carbon atom(s) and stable than then conjugate base of the para ✓acidic than para-hydroxyacetophenone.
- 1. Rank the following species in order of increasing acidity. Explain your reasons for ordering them as you do. HF NH3 H2SO4 CH3OH CH3COOH H3O+ H2O2. Consider the following compounds that vary from nearly nonacidic to strongly acidic. Draw the conjugate bases of these compounds, and explain why the acidity increases so dramatically with substitution by nitro groups. CH4 CH3NO2 CH2(NO2)2 CH(NO2)3H₂NNH₂/NaOH HO LOH/ catalytic NaOH (No acid or heat) 1) 1.0 cq, LDA 2) 3) H₂0 1) catalytic NaOH 2) H₂0 heat 1) 1.0 eq. NaOH 2) H₁0 heatHighlight in red each acidic location on the organic molecule at left. Highlight in blue each basic location on the organic molecule at right. Note for advanced students: we mean acidic or basic in the Brønsted-Lowry sense only. H,N ОН OH ни Он OH x с
- 9. Which of the compounds listed below is more acidic than 1-butanol? a) Diethylmalonate b) 2-Butanone c) Ethyl pentanoate d) All of these choices. e) Two of these choices. 11. Circle the Roman numeral corresponding to the most acidic hydrogen in the molecule below. III ve Î IV I II 10. Which of the compounds listed below is more acidic than 2- pentanol? a) Ethyl 3-oxopentanoate b) 2-Pentanone c) Pentanal d) All of these choices. e) Two of these choices. 12. Which of the following represent keto-enol tautomers? a) || CH3CCH₂CH3 and b) OH I CH₂=CCH₂CH3 c) HOCH₂CCH=CH₂ and and OH I CH3C=CHCH3 i CH3CCH₂CH3 CH3CCH₂CH3Parts A and B A. Circle the molecule with rhe lowest bp. HO- HO, B. Rank from most acidic (1) to least acidic (4) phenol p-nitrophenol p-methylphenol tert-butanolShow the steps necessary to transform the acid on the left into the compound on the right. Be sure to use SOCl2. CH сн,сен,сон > сносн сносн,
- For each of the above, laborios a) Write "most" under the compound which is most basic. Write "least" under the compound which is least basic. ANH CH NH₂ b) Write "highest" under the compound with the highest boiling point. Write "lowest" under the compound with the lowest boiling point. CH3 H₂C CH₂ CH₂ H₂N H₂N CH₂ H₂c مع ملی c) Write "most" under the compound which is most easily hydrolyzed to the acid. Write "least" under the compound which is least easily hydrolyzed to the acid.2. Draw the products using curved arrows for the following acid base reaction. Label its conjugated acid-base pair. I—Z Base + N H. Acid H H seEtONaas 2. In each pair, circle the stronger base. Strong booses a) EtOH EtONa EtONaCam cecct asoEid -Na, NHe(Anine>), b NANH2 c) tBuOK NaH the following