Problem_Set_5_KEY - a. b. Br N O CN NaCN H 3 O + O OH SOCl...

Info iconThis preview shows pages 1–7. Sign up to view the full content.

View Full Document Right Arrow Icon
Problem Set #5: Chapter 21 1. Proviide the name or the structure for the following compounds Cl O benzoyl chloride O O O acetic isopropanoic anhydride O O phenyl benzoate N H O N-methyl-2 cyclohexene carboxamide ethyl-cyclopropane carboxylate O O
Background image of page 1

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

View Full DocumentRight Arrow Icon
2. Provide the products and/or the conditions for the following transformations. O O CH 3 OH H + O OH O OH O 1. SOCl 2 2. CH 3 NH 2 NH O HO O 1. CH 3 OH, H + 2. DIBAL-H, -78 o C 3. H 3 O + H O NH 2 O 1. H 2 O, H + 2. SOCl 2 3. CH 3 COONa O O O O O O OCH 3 O HO O CH 3 OH OCH 3 O N H O CH 3 CH 2 NH 2 heat
Background image of page 2
O O OH O 1. H 3 O + 2. CH 3 OH, H + 1. H + , H 2 O 2. SOCl 2 3. CH 3 CH 2 CO 2 Na H 3 O + heat heat O HO O N O O O O O O O O HO O NH 3 O O O O HO O CH 3 NH 2 1. NaOH, H 2 O 2. H + N O N H OH O
Background image of page 3

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

View Full DocumentRight Arrow Icon
3. Provide a reasonable mechanism for the following transformations: a. HO OH O O O + H 2 O H + HO OH OH O OH HO H proton transfer O O HO H H O O H b. O O CH 3 NH 2 heat N H O OH NH 2 O N H H O proton transfer O N H OH N H O O H
Background image of page 4
4. Provide a reasonable synthesis for the following molecules using the given starting material and any other carbon contaning compound you need with 2C atoms or less
Background image of page 5

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

View Full DocumentRight Arrow Icon
Background image of page 6
Background image of page 7
This is the end of the preview. Sign up to access the rest of the document.

Unformatted text preview: a. b. Br N O CN NaCN H 3 O + O OH SOCl 2 O Cl H N (2 eq) NO 2 O O CH 3 Cl AlCl 3 KMnO 4 NaOH OH O OH O NO 2 H 2 SO 4 HNO 3 Cl O NO 2 SOCl 2 CH 3 CH 2 OH 5. Determine the structure of the following compounds based on their 1H-NMR spectra: a. C 9 H 9 OCl IR: 1800 cm-1 1H NMR: 7.30-7.40 ppm (multiplet, 5H); 3.17 ppm (d, 2H); 2.95 ppm (d, 2H) 1 2 3 4 5 6 7 8 PPM 5 2 2 Cl O b. C 7 H 12 O 3 IR: 1720 cm-1 ; 1740 cm-1 ; 1200 cm-1 1H NMR: 4.21 ppm (q, 2H); 3.36 ppm (q, 1H); 2.31 ppm (s, 3H); 1.29 ppm (t, 3H); 0.90 ppm (d, 3H) 1 2 3 4 5 PPM 3 1 2 3 3 O O O...
View Full Document

Page1 / 7

Problem_Set_5_KEY - a. b. Br N O CN NaCN H 3 O + O OH SOCl...

This preview shows document pages 1 - 7. Sign up to view the full document.

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