Final Review - ORGANIC SYNTHESIS CH3CH3 H3C O NH CH3 To...

Info iconThis preview shows pages 1–3. Sign up to view the full content.

View Full Document Right Arrow Icon
1 ORGANIC SYNTHESIS: CH 3 CH 3 Æ Æ Æ C H 3 NH CH 3 O To produce an amide, we need an amine plus either an ester or an acid halide. To produce the amine from ethane: 1) CH 3 CH 3 + Cl 2 /h ν CH 3 CH 2 Cl + HCl (substitution reaction or halogenation) (ethane) (chloroethane) 2) CH 3 CH 2 Cl + NH 2 CH 3 CH 2 NH 2 + Cl (substitution reaction) (chloroethane) (ethanamine/ethylamine) To produce an ester from ethane: 1) CH 3 CH 3 + Cl 2 /h ν CH 3 CH 2 Cl + HCl (substitution reaction or halogenation) (ethane) (chloroethane) 2) CH 3 CH 2 Cl + OH CH 3 CH 2 OH + Cl (nucleophilic substitution reaction) (chloroethane) (ethanol) 3) CH 3 CH 2 OH + Cr 2 O 7 2– /H + CH 3 COOH (oxidation) (ethanol) (ethanoic acid) 4) CH 3 COOH + CH 3 CH 2 OH + H + CH 3 C(O)OCH 2 CH 3 + H 2 O (substitution reaction or (ethanoic acid) (ethyl ethanoate) condensation reaction) To produce an acid halide: 1) CH 3 CH 3 + Cl 2 /h ν CH 3 CH 2 Cl + HCl (substitution reaction or halogenation) (ethane) (chloroethane) 2) CH 3 CH 2 Cl + OH CH 3 CH 2 OH + Cl (nucleophilic substitution reaction) (chloroethane) (ethanol) 3) CH 3 CH 2 OH + Cr 2 O 7 2– /H + CH 3 COOH (oxidation) (ethanol) (ethanoic acid) 4) CH 3 COOH + SOCl 2 CH 3 C(O)Cl + HCl + SO 2 (substitution reaction) (ethanoic acid) (acetyl chloride) To produce the amide: CH 3 C(O)OCH 2 CH 3 + CH 3 CH 2 NH 2 C H 3 NH CH 3 O + HOCH 2 CH 3 (substitution reaction) CH 3 C(O)Cl + CH 3 CH 2 NH 2 C H 3 NH CH 3 O + HCl (substitution reaction)
Background image of page 1

Info iconThis preview has intentionally blurred sections. Sign up to view the full version.

View Full Document Right Arrow Icon
2 Review Questions from Last Class: 1. CH 3 CH(CH 3 )CHCH 2 + ?? CH 3 CH(CH 3 )CH(Br)CH 3 2. What is the most likely major product when 2-methylpentane is treated with Br 2 /h v ? 3. What is the product of the oxidation of 2-propanol? 4. What is the product of the reaction of the following with H 2 O/H 2 SO 4 ? i) 1-methylcyclopentene ii) CH 2 5. What is the product of 1-bromo-3-methylbutane + NaOH? 6. i) ii) benzaldehyde + ethanol 7. Which of the following are chiral? 8. Draw the Lewis structure for C 2 2– and give the formal charges for each carbon atom. 9. Draw the Lewis structure for nitrite ion, give the formal charges and predict the shape. 10. How many sigma and pi bonds are present in H 3 CSCN? 11. A solution of bleach, sodium hypochlorite, labeled “0.030M NaClO”, had a pH of 10.00. Calculate K a for HClO. 12. Write NIE’s for the reactions that occur when perchloric acid and sodium hydroxide are added to a C 2 H 5 NH 3 Cl/C 2 H 5 NH 2 buffer.
Background image of page 2
Image of page 3
This is the end of the preview. Sign up to access the rest of the document.

{[ snackBarMessage ]}

Page1 / 7

Final Review - ORGANIC SYNTHESIS CH3CH3 H3C O NH CH3 To...

This preview shows document pages 1 - 3. Sign up to view the full document.

View Full Document Right Arrow Icon
Ask a homework question - tutors are online