10-01 - 10/1/2010 What is the product of the following...

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Unformatted text preview: 10/1/2010 What is the product of the following reaction sequence? H H OH Br Li H O What is the product of the following reaction sequence? H ? OH H Br Br Li Li H O H + H O Li Li O Br Li O Br Li A B C D E A B C D E 2 What is the product of the following reaction sequence? D H OH Br Br Li Li + D O Li Li D O D H hydrocarbons hydrocarbons are compounds containing only the th elements C and H. alkanes C C alkenes alkenes C C aromatics O Br D A B C D E 3 C—C and C—H bonds are notoriously unreactive. Why are they of interest to chemistry and biology? 1. Alkanes are the scaffolds upon which groups are attached to give functional molecules. HO HO O H H O cortisone, cortison e, a steroidal anti-inflammatory drug H HO HO O Choose the correct formula for the following structure: Nomenclature? H alkanes CnH2n+2 = C10H2(10)+2= C10H22 n = 10 C C 2. Hydrocarbons are very hydrophobic, they hate water. This property plays a very important role in the assembly of molecules to form functional structures. Any unambiguous name is acceptable. trimethylheptane A. C10H20 B. C10H18 2,3,6-trimethylheptane D. C10H16 E. C10H24 C. C10H22 1 10/1/2010 Choose the correct structure for the following formula: Choose the correct structure for the following formula: C19H30 What is the formula for a C19 alkane? CnH2n + 2 = C19H40 C19H30 What is the formula for a C19 alkane? CnH2n + 2 = C19H40 Hint: all structures contain 19 carbon atoms. Hint: all structures contain 19 carbon atoms. A C B D A C B D How many hydrogens are lost when a double bond forms? How many hydrogens are lost when a ring forms? How many rings + double bonds are present in C19H30? How many hydrogens are lost when a double bond forms? How many hydrogens are lost when a ring forms? formula for an acyclic, saturated hydrocarbon = CnH2n +2 formula for any hydrocarbon = CnH2n + 2 – 2(double bonds + rings) Which of the following structures have the formula C8H14? How does a chemical formulas change if the compound contains oxygen and/or nitrogen? O CH CH3 H H C C H H HH C H H CH CH3 C CH CH3 1 index index of hydrogen = 2 deficiency 2 3 C9H20 = C H3C C9H20 A. = 2 and 3 D. = 2 only B. = 1 and 3 E. = all C. = 3 only F. = none Hydrocarbons are rare in organic chemistry. How does this formula change when the structure contains oxygen and nitrogen? Hydrocarbons are rare in organic chemistry. How does this formula change when the structure contains oxygen and nitrogen? O CH CH3 H H C C H H HH C H H CH CH3 C CH CH3 CH CH3 H H C C H H HH C H H CH CH3 C CH CH3 = C9H20 C H3C = C9H20 C H3C C9H20 C9H20 When nitrogen is present the hydrocarbon contains one more hydrogen. OH OH O N H N H C9H20O, an ether C9H20O, an alcohol C9H21N, a 2° amine H C9H21N, a 1° amine 2 10/1/2010 What is the molecular formula of Cortisone? 20 OH 18 17 O 11 19 13 21 16 H 1 OH 9 14 12 2 10 4 5 O Choose the correct formula for the following bicyclic structure: = CnH2n+2 n=9 = C9H2(9)+2 – 2(2) = C9H16 - 2(number of rings) H 6 7 8 H 15 O3 cortisone = C21 H44 – 2(8)O5 = = C21H28O5 A. = C21H30O5 D. = C22H28O5 B. = C21H26O5 E. = C21H42O5 C. = C21H28O6 F. = C21H28O5 A. C10H20 B. C9H18 C. C10H22 D. C9H16 E. C10H18 Nomenclature: Choose the correct formula for the structure on the right: bridgehead constitutional isomers bicyclo 4.3.0] nonane [ 4.3.0 Which of the following structures have the formula C8H14O? HO HO HO HO HO HO O 1 A. = 2 and 4 D. = 3 and 4 2 3 B. = 1 and 4 E. = all 4 C. = 3 and 1 F. = none A. bicyclo[4.3.0]nonane C. bicyclo[2.2.0]nonane B. bicyclo[4.3.0]nonane D. bicyclo[3.2.2] nonane Conformational Analysis. The shape of molecules. Chymotrypsin primary structure tertiary structure What are the possible shapes for ethane (C2H6)? H C H C H H H C HH C H H H HH C H A = yes B = no H 60º MASLWLLSCFSLVGAAFGCGV PAIHPVLSGLSRIVNGEDAVPG SWPWQVSLQDKTGFHFCGG SLISEDWVVTAAHCGVRTSDV VVAGEFDQGSDEENIQVLKIA KVFKNPKFSILTVNNDITLLKLA TPARFSQTVSAVCLPSADDDF PATLCATTGWGKTKYNANKTP DKLQQAALPLLSNAECKKSW GRRITDVMICAGASGVSSCMG DSGGPLVCQKDGAWTLVGIVS WGSDTCSTSSPGVYARVTKLI PWVQKILAAN HH C HH Are the above structures identical? isomers = compounds with the same formula but different structures. 3 ...
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This note was uploaded on 12/05/2010 for the course CHE 321 taught by Professor Fowler/sampson during the Fall '08 term at SUNY Stony Brook.

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