09-16 - 9/16/2009 Propose a synthesis of A from compounds...

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Unformatted text preview: 9/16/2009 Propose a synthesis of A from compounds containing H 4 carbon atoms or less. PCC H C C Br OH C OH C C C OH H 1. Li C Br 2. C O 3. H2O C Br C C O Propose a synthesis of A from compounds containing H 4 carbon atoms or less. PCC H C Br C Br OH C OH C C C OH H 1. Li C Br 2. C O 3. H2O C Br C C O Br C C H2 Pd/C C H C H C C OH C H2 Pd/C C H C H C OH 1 . Get a piece of blank paper. H O 2. Get a pencil with an eraser. 3. Identify the general reaction scheme of the last step. 4. Redraw the product as the reactant. 5. Modify the reactant to make it consistent with the reaction scheme. 6. Repeat steps 3-5 until the problem is solved. H O PCC 1. Li 2. CH2=O 3. H2O H Br 1. Li 2. CH2=O 3. H2O Br A B C Br A A PCC H Br 1. Li 2. CH2=O 3. H2O 1. Li 2. CH2=O 3. H2O OH 1. Li 2. CH2=O 3. H2O PCC H Br 1. Li 2. CH2=O 3. H2O Propose a synthesis of A from compounds containing H 4 carbon atoms or less. PCC H C C Br OH C OH C C C OH H 1. Li C Br 2. C O 3. H2O C Br C C O Propose a synthesis of A from compounds containing H 4 carbon atoms or less. PCC H C Br C Br OH C OH C C C OH H 1. Li C Br 2. C O 3. H2O C Br C C O Br C C H2 Pd/C C H C H C C OH C H2 Pd/C C H C H C OH H O PCC OH 1. Li 2. C = O 3. H2O H O PCC OH 1. Li 2. CH2=O 3. H2O H 1. Li 2. CH2=O Br 3. H2O OH Br Br A A The The students shown on the right have entered their University ID numbers incorrectly on their eInstruction accounts. As a consequence, these students are not recognized and do not not receive credit for their clicker quiz participation 321 01 Michael Yoon Yanique Bailey Zanab Mian Student 214 Student 415 Marybeth Valenti Keisha Fraser Student 579 Ian Warslie Min Kim 321 02 Nicholas Chakiryan Grace Kim Student 384 Brittany Harvey Student 454 Ewuramm Boah Aditya Agarwal The interaction of light with matter. 4 78 111 214 415 437 467 579 604 23 electromagnetic electromagnetic radiation radiation + - visible light 297 343 384 434 454 463 474 5 1 9/16/2009 Choose the correct statement about light. electromagnetic electromagnetic radiation radiation + The interaction of light with matter. electromagnetic radiation radiation + wave wave length ( ) high energy - frequency frequency ( in cm) = ¯ =  low energy visible light A. A. Blue light has more energy and a longer wave length than red. more energy longer B. B. Blue light has more energy and a shorter wave length than red. more energy shorter short wavelength visible light long wavelength less energy shorter C. C. Blue light has less energy and a shorter wave length than red. D. D. Blue light has less energy and a longer wave length than red. less energy longer The interaction of light (energy) with molecules. wave wave length ( ) + Choose the statement that best describes why the sweater on the right absorbs blue light and causing the sweater to appear red. A. A. The atoms in bonds of the red dye absorb light energy by vibrating at a faster rate. high energy short wavelength frequency frequency ( in cm) = ¯ =  low energy long wavelength visible visible light O N N S O O O O S re d y e # 4 0 r e d dye #40 O B. B. The electrons in the red dye absorb light energy by being transferred into high energy anti bonding orbitals. C. The molecules of the red dye absorb light energy by rotating faster. D. The molecules the red dye absorb light energy by moving faster. electronic spectroscopy (color) O N N S O O O O electronic spectroscopy (color) O N N S O O O O N N S O O antibonding antibonding molecular orbital O S red dye #40 O S red dye #40 O blue light O O S re d d y e # 4 0 O O N N S O O O O * Orbital Energy bonding bonding molecular orbital S red dye #40 O 12 12 2 9/16/2009 Choose Choose the statement that best describes why the sweater on the right absorbs blue light and causing causing the sweater to appear red. A. The atoms in bonds of the red dye absorb The light energy by vibrating at a faster rate. Choose the statement that best describes why Choose the sweater on the right absorbs blue light and causing the sweater to appear red. A. A. The atoms in bonds of the red dye absorb light energy by vibrating at a faster rate. visible visible light visible visible light B. The electrons in the red dye absorb light energy by being The transferred into high energy anti bonding orbitals. C. The C. The molecules of the red dye absorb light energy by rotating faster. D. The D. The molecules the red dye absorb light energy by moving faster. Infrared Spectroscopy A. The atoms in bonds of the red dye absorb The light energy by vibrating at a faster rate. A model for a chemical bond (A B). Morse Curve. quantized vibrational states en energy visible light =1 =0 bond length AB A rAB AB B A 16 B The The interaction of light with molecules. Infrared Spectroscopy. Spectroscopy. quantized quantized vibrational states The The energy required to excite a vibration depends upon the the strength of the bond and the mass of the atoms. quantized vibrational states vibrational continuum en energy =1 =0 en energy =1 rAB AB =0= h infrared infrared energy source =0 rAB AB h 3 9/16/2009 The The energy required to excite a vibration depends upon the the strength of the bond and the mass of the atoms. Given that a C=C bond stretch occurs at 1640 cm-1, select select the the value that you would predict for a C C. A. 940 cm-1. B. 1062 cm-1. C. 1405 cm-1. D. 2115 cm-1. wave length ( ) Any molecule has 3n-6 vibrational modes where 3n- vibrational modes n = number of atoms present in the molecule. number energy frequency frequency ( in cm) = ¯ =  19 20 How many vibrational modes would be predicted for formaldehyde (CH2=O)? Any molecule has 3n-6 vibrational modes where 3n- vibrational modes n = number of atoms present in the molecule. number 1750 cm-1 1165 cm-1 A. 3 B. 6 C. 8 D. 20 E. 32 F. >32 3n-6 = number of vibrational modes 3n-6 = 3(4)  6 = 6 21 Why is the C=O bond the most intense? + - electromagnetic radiation How How many vibrational modes would be predicted for modes ibuprofen? ibuprofen? OH 1750 cm-1 1165 cm-1 C13H18O2 O 3(33) ibuprofen 3n ibuprofen = 3n  6 = 3(33)  6 = 93 vibrational vibrational modes A. 3 B. 6 C. 8 D. 20 E. 32 F. >32 25 4 9/16/2009 Which Which functional group in ibuprofen is responsible for the strong strong absorption at 1721 cm-1? C-H C-H =C=C-H O-H CO2H CC C=C C=O N-H CN 3000 A. C-H C- B. C=O C. C=C D. O-H O- E. C-C C- 4000 A. C-H C- B. C=O 2000 C. C=C cm-1 1500 D. O-H O- 1000 E. C-C C- 600 OH O O OH * 26 * 27 28 29 Do all C-H bonds have the same strength? CCC C-H C=C p s energy 2000 cm-1 1500 1000 -C-H =C=C-H C-H high energy 4000 3000 low energy 600 Which of the following has the C-H bonds correctly assigned C- bonds to the above infrared absorptions: , and ? Csp H1s H Csp2 H1s H Csp3 H1s H A. A. C. C. E. E. C-H -C-H =C=C-H =C=C-H C-H -C-H -C-H =C=C-H C-H B. B. D. D. F. F. C-H -C-H =C=C-H -C-H =C=C-H C-H =C=C-H C-H -C-H A. A. C-H =C=C-H -C-H increasing increasing strength of of the C-H bond C- 5 9/16/2009 CC C-H C=C C-H -C-H =C=C-H O-H CO2H CC C=C C=O N-H 4000 3000 2000 cm-1 1500 1000 600 4000 3000 CN 2000 cm-1 1500 1000 600 Which of the following has the C-H bonds correctly assigned C- bonds to the above infrared absorptions: , and ? A. A. C. C. E. E. C-H -C-H =C=C-H =C=C-H C-H -C-H -C-H =C=C-H C-H B. B. D. D. F. F. C-H -C-H =C=C-H -C-H =C=C-H C-H =C=C-H C-H -C-H A. A. C-H =C=C-H -C-H C-H -C-H =C=C-H O-H CO2H CC C=C C-H -C-H =C=C-H CC C=C C=O orgchem web site O-H (s) CO2H C=O(s) N-H 4000 3000 CN 2000 cm-1 1500 1000 600 4000 N-H 3000 CN 2000 cm-1 Which Which structure is consistent with the following ir spectrum? 1000 600 1500 C=O overtone ? ? O OCH3 OH OH OH OH O O A B C D C-H -C-H =C=C-H O-H CO2H CC C=C C-H -C-H =C=C-H CC C=C C=O N-H 4000 3000 O OH O OH CH3 CN 2000 cm-1 Which Which structure is consistent with the following ir spectrum? 1500 1000 600 4000 O-H CO2H C=O N-H 3000 CN 2000 O Which Which structure is consistent with the ir spectrum? 1500 1000 600 cm-1 O O OH OH O CH3 O O OH A OCH3 O D OH O D OH OH O OCH3 OCH3 O OCH3 A B OCH3 C B C OCH3 6 9/16/2009 C-H -C-H =C=C-H O-H CO2H CC C=C C=O N-H 4000 3000 CN 2000 cm-1 Which Which structure is consistent with the ir spectrum? 1500 1000 600 OH O OH CH3 O O O OH A OCH3 O OH OCH3 O OCH3 D B C Choose Choose the compound consistent with the above ir spectrum. spectrum. A B C D O O H Choose Choose the compound consistent with the above ir spectrum. spectrum. A B O C D OH O OH OH Choose Choose the compound consistent with the above ir spectrum. spectrum. A B O H C D OH O OH OH Some synthetic problems: Using the following reactions, propose syntheses for the following compounds from reactants containing four carbon atoms or less. H H H H C C Br OH C C Propose a synthesis of the following compound from reactants containing 4 carbon atoms or less. C OH H PCC Br C C O Br C OH C C Br OH C C C OH H PCC Br C C C O Br C H2 Pd/C C H C H C Br 1. Li 2. C O 3. H2O C C OH C H2 Pd/C C H C H C OH Br H2 OH C C 1. Li Br 2. C O 3. H2O C C OH Pd/C H O Br 42 Br OH 1. Li Br 2. O 43 7 9/16/2009 O 1. H Br Br OH 2. H2O Li OH Br 1. 2. H2O H Br Br OH Li O 44 45 1. Li OH O PCC OH 2. Br 3. H2O H H HO 1. Li 2. CH2=O 3. H2O Br Br Br Br HO 46 8 ...
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