09-23 - 9/24/2009 Are there other acid base reactions in...

Info iconThis preview shows page 1. Sign up to view the full content.

View Full Document Right Arrow Icon
This is the end of the preview. Sign up to access the rest of the document.

Unformatted text preview: 9/24/2009 Are there other acid base reactions in organic chemistry that do not involve H transfer? + H Cl + Are there other acid base reactions in organic chemistry that do not involve H transfer? Choose the answer that has the acid and base correctly identified. A. I = acid, II = acid C. I = base, II = acid B. I = base, II = base D. I = acid, II = base H O H O H Cl E. Neither I or II is an acid or base base acid H H O + C HH Cl HO H C HH + Cl H H + HH H HO C HH H + Cl O I C II Cl 1 H OC HH Cl + 2 Which species is the acid in the following reaction? Which species is the acid in the following reaction? H H C H C H + H H H B H H H B C H H H H B C H H C H H 3 H H C H H H C H C H H H H H B C H C H 4 H + H B H H H H B C H H C H H A B H Which species is the acid in the following reaction? Use the curved arrow formalism to show the bond making and bond breaking that occurs in the transformation of the following reactants to the product. H H C H C H H H H B C H H C H 5 CH3 H2C C CH3 H CH3 H H3C C CH3 C C CH3 CH3 H + H B H H H H B C H H C H H H 6 1 9/24/2009 Use the curved arrow formalism to show the bond making and Use bond breaking of the first step of the following reaction. Choose the structure of product of the first step. CH3 H2C C CH3 Use the curved arrow formalism to show the bond making and Use bond breaking of the first step of the following reaction. H CH3 ? H2C C CH3 H H H2C C CH3 CH3 Is a carbocation an (A) acid or (B) base? CH3 H2C C H H3C C CH3 CH3 CH3 CH3 H H3C C CH3 C C CH3 CH3 H3C CH3 H C CH3 C C CH3 CH3 A B 7 8 Use the curved arrow formalism to show the bond making and bond breaking of each step of the following reaction. Add formal charges to the atoms to make the structures correct. CH3 CH3 H2C C CH3 H CH3 H3C C CH3 H2C C CH3 Propose a good synthesis of the following alcohol. H H OH 1. Li 2. C=O 3. H2O C C H2 Pd/C C H C H C Br C C Br OH C C C C OH H PCC Br C C O Br OH 1. Li 2. C O 3. H2O C C OH CH3 H H3C C C C CH3 H CH3 CH3 -H H3C CH3 H C CH3 C C CH3 CH3 9 Propose a good synthesis of the following alcohol. Propose a good synthesis of the following alcohol. H H OH 1. Li 2. C=O 3. H2O C C H2 Pd/C C H C H C Br C C Br OH C C C C OH H PCC Br H C C O Br 1. Li 2. 3. H2O H OH C C Br OH C C C C OH H PCC Br C C O Br OH OH 1. Li 2. C O 3. H2O C C OH O C C H2 Pd/C C H C H C Br 1. Li 2. C O 3. H2O C C OH OH Br O 2 9/24/2009 Propose a good synthesis of the following alcohol. Predict the product of the following reaction. H H OH 1. Li 2. 3. H2O O C C H2 Pd/C C H C H C Br C C Br OH C C C C OH H PCC Br H C C O Br 1. Li 2. 3. H2O H OH C C Br OH C C C C OH H PCC Br C C O Br OH OH 1. Li 2. C O 3. H2O C C OH O C C H2 Pd/C C H C H C Br 1. Li 2. C O 3. H2O C C OH Br H Br Br H Br OH OH 14 Predict the product of the following reaction. Predict the product of the following reaction. H H H OH 1. Li 2. 3. H2O O C C H2 Pd/C C H C H C Br C C Br OH C C C C OH H PCC Br H C C O Br OH Br Li H O ? H C C C C OH H 1. Li C Br 2. C O 3. H2O C C OH Br OH OH H PCC C 1. Li 2. C O 3. H2O C C OH C C Br OH C C O Br C H2 Pd/C C H C H Br H Br 1. Li 2. CH2=O 3. H2O OH Br CH2 OH O 15 O Br Li A B C D E 16 Predict the product of the following reaction. H H OH Br Br Li Li + H O Li Li H O H 2-methylheptadecane H hydrocarbons hydrocarbons are compounds containing only the elements C and H. alkanes C C O Br Li A B C D E 17 18 3 9/24/2009 C C and C H bonds are notoriously unreactive. Why are they of interest to chemistry and biology? alkanes alkenes alkenes aromatics O cortison cortison e, a steroidal anti-inflammatory drug H C C hydrocarbons hydrocarbons are compounds containing only the elements C and H. 1. Alkanes are the scaffolds upon which groups are alkanes attached to give functional molecules. HO HO O H H H HO HO O H C C C C 19 2. Hydrocarbons are very hydrophobic, they hate water. This property plays a very important role in the assembly of molecules to form functional structures. 20 Choose the correct formula for the following structure: Nomenclature? CnH2n+2 = C10H2(10)+2= C10H22 n = 10 Any unambiguous name is acceptable. trimethylheptane A. C10H20 B. C10H18 2,3,6-trimethylheptane D. C10H16 E. C10H24 21 What is the index of hydrogen deficiency? alkane formula = CnH2n+2 cycloalkane formula = CnH2n+2 - 2(number of rings) H HH HH H HCCCH H HCCCH H HH HH H H HCCCH H HCCCH H HH -2H C. C10H22 C18H38 = alkane C18H38-8 = C18H30 = cycloalkane What is the index of hydrogen deficiency? alkane formula = CnH2n+2 cycloalkane formula = CnH2n+2 - 2(number of rings) alkene formula = CnH2n+2 - 2(number of double bonds) What is the index of hydrogen deficiency? alkane formula = CnH2n+2 cycloalkane formula = CnH2n+2 - 2(number of rings) alkene formula = CnH2n+2 - 2(number of double bonds) any hydrocarbon formula = alkane formula (CnH2n+2) lk (C alkanes cycloalkanes alkenes alkynes HH H H C H C C HH C C HH H C H H HH -2H H H H H C H C C H H C H C H C C H H C C HH H C H H HH -2(number of rings + number of double bonds) H C H C C6H14 = alkane C6H14-6 = C6H8 = alkene index of hydrogen deficiency = number of rings + number of double bonds 24 4 9/24/2009 What is the index of hydrogen deficiency and formula of the following compound? Which of the following structures have the formula C8H14? index of hydrogen = 1 ring + 1 double bond = 2 deficiency formula = C8H18- 2(2) = C8H14 1 index index of hydrogen = 2 deficiency 2 3 A. B. B. C. C. D. D. E. E. 0 1 2 3 2 C8H14 C8H16 C8H14 C8H16 C8H18 25 A. A. = 2 and 3 D. D. = 2 only B. = 1 and 3 B. E. = all E. C. = 3 only F. = none 26 5 ...
View Full Document

Ask a homework question - tutors are online