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Organic Chemistry

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  1. Organic Chemistry Tutorial

  2. This presentation is completely interactive • In order for this presentation to work you MUST follow the indicated tabs on each slide • Answer the question on a separate piece of paper and compare with the slides • This presentations purpose is to try and find what you haven’t understood or what you haven’t attempted • Follow it properly and you will succeed! Notes on Presentation NEXT SLIDE

  3. IUPAC, The International Union of Pure and Applied Chemistry, is a worldwide organization which was established in1918. It’s main purpose is to aid in chemical sciences as well as their applications with humankind. Organic nomenclature, being a large focus of IUPAC, was established in 1892 when chemists created a list of rules called the Geneva rules. This group of chemists ultimately became IUPAC and is who we should thank for organic nomenclature. IUPAC NEXT SLIDE

  4. IUPAC has 4 fundamental steps when naming organic compounds. The following steps should be considered: • (1) Identify and name the parent chain. • The Parent Chain is usually the single largest continuous chain of carbon atoms within an organic molecule. Its name is dependent on the number of carbon atoms. Its name should be determined by the following prefixes. IUPAC Nomenclature Rules NEXT SLIDE

  5. Parent Chain Prefixes NEXT SLIDE

  6. (2) Identify and name the substituent’s. • The Substituent’s are the chain like • projections from the parent chain. • The majority of these chains follow • the parent chain prefixes. They contain the • Suffix “yl” added to the prefix. You can see that the longest possible chain is 9 without the incorporation of the 2 carbon chain. This is an example of a substituent. IUPAC Nomenclature Rules NEXT SLIDE

  7. (3) Number the parent chain and assign a locant to each substituent. • A Locant is the carbon number of the substituent attached to the parent chain. It is important that you number a parent chain such that the sum of all locant’s is the least possible. This standard is used to prevent the same molecule being named twice simply by false numbering. IUPAC Nomenclature Rules NEXT SLIDE

  8. (4) Assemble the substituent's in alphabetical order. • You should only consider the alphabetical order of the parent chain prefix, not additional sub-prefixes (di, tri, etc.) which are attached to the beginning of a prefix for a substituent if there exist more than one on a parent chain of the same type. • Know that you have the 4 fundamental IUPAC steps… • Let’s start naming! IUPAC Nomenclature Rules NEXT SLIDE

  9. Alkanes are organic compounds that contain fully saturated parent chains. That is, they are the hydrocarbons that contain the most hydrogen atoms possible (No Double or Triple Bonds). These molecules contain Sigma bonds between all C-C Bonds. When naming alkanes, the suffix “ane” is attached to the parent chain prefix. Alkanes NEXT SLIDE

  10. Cycloalkanes are the alkanes which exhibit a ring structure. These molecules will contain the “cyclo” suffix added to the parent chain prefix if the parent chain being considered is the ring structure. The “cyclo” suffix can also be conjoint with the parent chain suffix if considered an Alykl Group (substituent's that are of alkane essence). For the second case, the parent chain will be named as normal alkanes. Cycloalkanes NEXT SLIDE

  11. QUESTION: • Name the following Organic Molecule: Question Section NEXT QUESTION ANSWER HELP

  12. ANSWER: • STEP 1: Identify and name the parent. • Since there are 6 carbons there, the parent name should be hexane. And since there are no substituent's, there is not need to follow the next 3 steps. • ANSWER: Hexane Question Section NEXT QUESTION ANSWER HELP

  13. (2) QUESTION: • Name the following Organic Molecule in two ways: Question Section NEXT QUESTION ANSWER HELP

  14. (2) ANSWER: • Consider the Cycloalkane as the Parent • STEP 1: Identify and name the parent. • The parent is the 6 carbon atom cycloalkane. Which should be named cyclohexane. • STEP 2: Identify and name the substituent's. • The only substituent's is an 5 carbon atom alkyl group. Which should be name pentyl. • Since the other two steps aren’t required for this molecule we achieve a name of • ANSWER: Pentyl Cyclohexane Question Section NEXT QUESTION ANSWER HINT

  15. (2) ANSWER: • Consider the Alkane as the Parent • STEP 1: Identify and name the parent. • The parent is the 5 carbon atom alkane. Which should be named pentane. • STEP 2: Identify and name the substituent's. • The only substituent's is the 6 carbon cycloalkane. Which should be name cyclohexyl. • Since the other two steps aren’t required for this molecule we achieve a name of • ANSWER: 1 - Cyclohexyl Pentane Question Section NEXT QUESTION ANSWER HELP

  16. (3) QUESTION: • Name the following Organic Molecule: Question Section NEXT QUESTION ANSWER HINT

  17. (3) ANSWER: • STEP 1: Identify and name the parent. • The parent chain is the 7 carbon chain • Which should be named HEPTANE. • STEP 2: Identify and name the substituent's. • The two substituent's that exist are ETHYL and the CYCLOHEXYL • STEP 3: Number the parent chain and assign a locant to each. It is clear by the diagrams below that the best option is 1 for cyclohexyl and 4 for • Ethyl since the sum is less than 4 and 7. • STEP 4: Alphabetize • ANSWER: 4-ETHYL-1-CYCLOHEXYLHEPTANE Question Section 2 4 6 6 4 2 1 3 5 7 7 5 3 1 NEXT QUESTION ANSWER HELP

  18. QUESTION: • Alkanes are typically straight chain molecules due to the alignment • of sigma bonds. Question Section NEXT QUESTION ANSWER HINT

  19. (4) ANSWER: • Alkanes aren’t typically straight chain molecules. Straight chain • molecules are due to the overlapping of pi bonds and are usually • found in alkynes. • ANSWER: FALSE Question Section NEXT QUESTION ANSWER HELP

  20. The following structures have special names associated with their type of bonding: Complex Substituents Phenyl Isopropyl Sec-Butyl Tert-Butyl Isobutyl 3-Carbon 4-Carbon Benzene NEXT SLIDE

  21. These substituents are those in the halogen column of the periodic table: Alkyl Halides Fluoro Chloro Bromo Iodo NEXT SLIDE

  22. Alkenes are organic compounds that contain at least one unsaturated carbon. That is, they are the hydrocarbons that contain at least one double bond. These molecules contain Sigma bonds between all C-C Bonds and a Pi bond between all C=C. When naming alkenes, the suffix “ene” is attached to the parent chain prefix as well as the appropriate location of the double bond. Alkenes NEXT SLIDE

  23. Alkynes are organic compounds that contain at least one triple bond. These molecules contain Sigma bonds between all C-C Bonds and a 2 Pi bond between all C≡C. When naming alkynes, the suffix “yne” is attached to the parent chain prefix as well as the appropriate location of the triple bond. Alkynes NEXT SLIDE

  24. (5) QUESTION: • Name the following Organic Molecule: Question Section NEXT QUESTION ANSWER HINT

  25. (5) ANSWER: • STEP 1: Parent chain is 10 Carbons long which must include the triple • bond. We will include the double bond as a side chain for ease of • naming and since the triple bond has that higher authority. • STEP 2: 4 substituents (3 alkyl halides: 2 chlorines and 1 fluorine, 1 • double bond ethyl side chain) • STEP 3: Chloro at 7 and 9 (must count from the carbon • closest to the triple bond) , Fluoro at 6, allyl (the name for the ethyl • double bond) at 8. • STEP 4: Alphabetize (allyl, dichloro, fluoro) • ANSWER: 8-allyl-7,9-dichloro-6-fluoro-2-decyne Question Section NEXT QUESTION ANSWER HELP

  26. (6) QUESTION: • Count the number of carbon’s, • Hydrogens. • Name this molecule. Question Section NEXT QUESTION ANSWER HINT

  27. (6) ANSWER: • STEP 1: Parent chain is 9 Carbons long which must • include the double bond. • STEP 2: 4 substituents (1 alkyl halide, 1 Tert Butyl, • 1 alkyl, 1 cycloalkyl) • STEP 3: iodo at 7, tert Butyl at 6, methyl at 3, • Cyclohexyl at 2. • STEP 4: Alphabetize (tert Butyl, cyclohexyl, Iodo, • methyl) • ANSWER: 6-tert Butyl-2 cyclohexyl-7-iodo-3 methyl-1,3-nondiene (20 CARBONS, 33 HYDROGENS) Question Section NEXT QUESTION ANSWER HELP

  28. (7) QUESTION: • Name this molecule: Question Section NEXT QUESTION ANSWER HINT

  29. (7) ANSWER: • STEP 1: Parent chain is 7 Carbons long. • STEP 2: 6 substituents (4 phenol, 2 alkyl halides) • STEP 3: Phenyl at 1,2,6,7 and chloro at 3,5. • STEP 4: Alphabetize (chloro, phenyl) • ANSWER: 3,5-dichloro-1,2,6,7-tetraphenyl-heptane Question Section NEXT QUESTION ANSWER HELP

  30. Alcohols are organic compounds that contain an OH, hydroxyl group, and are named according to an ending in “ol”. • Phenols are alcohols comprised of a hydroxyl group attached directly to a phenyl ring. • When numbering the parent chain, alcohol should receive lowest numbering despite presence of alkyl substituent's or pi bonds. Alcohols and Phenols NEXT SLIDE

  31. Ethers are compounds that contain an oxygen atom bonded between two R groups, where each R group can be an alkyl, aryl (aromatic compounds like benzene), or vinyl (double bonded side chains). • Two methods of naming: • Name the 2 substituents alphabetically followed by “Ether” • Place “oxy” between a side chain and a parent chain respectively. Ethers NEXT SLIDE

  32. Epoxides are cyclic ethers that contain an oxygen within a cycloalkane. A special type is Oxirane, which is the triangular epoxide that is more reactive than other ethers due to a significant ring strain. • When naming as parents use the following Parent Chains: Epoxides When naming as side chain, merge epoxy with the position of the “overlapping carbons”. Oxane Oxirane Oxetane Oxolane NEXT SLIDE

  33. (8) QUESTION: • Name this molecule in two ways: Question Section NEXT QUESTION ANSWER HINT

  34. (8) ANSWER: • OPTION 1 • Sides chains are butyl and pentyl • Thus: Butyl Pentyl Ether • OPTION 2 • Take Pentane as the Parent chain and Butyl as the side chains • Thus: Butoxypentane • ANSWER: Butyl Pentyl Ether Butoxypentane Question Section NEXT QUESTION ANSWER HELP

  35. (9) QUESTION: • Name all the following molecules. Using your knowledge from • previous chemistry courses, order the following molecules in order • of increasing boiling point. Question Section NEXT QUESTION ANSWER HINT

  36. (9) ANSWER: • Compound 1: 1-Butanol • Compound 2: 1,4-Butandiol • Compound 3: butane • Compound 4: methoxyethane • ANSWER: Butane < Methoxyethane < 1-Butanol < 1,4-Butandiol 1 hydrogen bond interaction per molecule Question Section 2 hydrogen bond interactions per molecule No hydrogen bonds no major electronegative change Slight electronegative change between the oxygen atom and carbon atoms, creates dipole on the oxygen. NEXT QUESTION ANSWER HELP

  37. (10) QUESTION: • Name all the following molecule: Question Section NEXT QUESTION ANSWER HINT

  38. (10) ANSWER: • STEP 1: Parent chain is 12 carbons long with • A triple bond, thus dodecyne. • STEP 2: There are 5 substituents (2 isopropyl, • 1 epoxy, 1 phenyl, 1 methyl) • STEP 3: isopropyl is at the 6 and 9 position, • The epoxy at 7 and 8, phenyl at 10 and methyl at 2. • STEP 4: Alphabetize (epoxy, isopropyl, methyl, phenyl) • ANSWER: Butane < Methoxyethane < 1-Butanol < 1,4-Butandiol Question Section NEXT QUESTION ANSWER HELP

  39. Since Sulphur is under oxygen in the periodic table, it is often the case the oxygen contain organic molecules will have a sulphur derivative. Alcohols, oxygen bound to hydrogen and carbon, is referred to as a THIOL when replaced with sulphur. Add the term “thiol” to the parent chain for SH containing molecules. If other functional groups are present, use “mercapto” as the substituent name. Ethers, oxygen bound to two carbons on either side, is referred to as a SULFIDE when replaced with sulphur. Replace “sulfide” with ether or replace “ylthio” with “oxy” for parent chains and substituents respectively. Thiols and Sulfides NEXT SLIDE

  40. Here are some examples of these molecules: Thiols and Sulfides Sulfides that undergo oxidation reactions are called Sulfoxide (for one oxygen) and Sulfone (for two oxygen) Ethylthioethane 1,4-Pentanedithiol Diethyl Sulfoxide Diethyl Sulfide Diethyl Sulfone 4,6-dimercapto-3-octyne NEXT SLIDE

  41. A CARBONYL group is an oxygen group double bonded to a Carbon. Within an organic molecule this can happen at two locations, First, the very end or very beginning of the molecule. This type of molecule is referred to as an ALDEHYDE. Attach the suffix “al” to the parent chain when naming. Use “carbaldehyde” when an aldehyde group is attached on the first carbon after a cyclic compound. Secondly, anywhere except the very end and the very beginning. This type of molecule is referred to as a KETONE. Attach the suffix “one” to the parent chain when naming. You may also use the method similar to ether, where you will place the parent name of each chain and followed by “ketone”. Aldehydes and Ketones NEXT SLIDE

  42. Here are some examples of these molecules: Aldehydes and Ketones Pentanal Methyl propyl ketone Cyclopentanecarbaldehyde 2-pentanone Formaldeyhde is a popular preservative as it has the ability to prevent the growth of common bacteria and fungi. It is the simplest form of aldehyde and is a significant consideration to human health as it may be carcinogenic. Methanal Formaldehyde NEXT SLIDE

  43. (11) QUESTION: • Name the molecule: Question Section NEXT QUESTION ANSWER HINT

  44. (11) ANSWER: • STEP 1: Parent chain is 7 Carbons long. • STEP 2: substituents ( 1 phenyl, 2 carbonyl groups, 1 thiol) • STEP 3: Phenyl at 3, Carbonyl groups at 2, 6, Thiol at 4. • STEP 4: Alphabetize (mercapto, phenyl) • ANSWER: 4-mercapto-3-phenyl-2,6-heptandial Question Section NEXT QUESTION ANSWER HELP

  45. (12) QUESTION: • Name all the following molecules. Using your knowledge from • previous chemistry courses, order the following molecules in order • of increasing boiling point. Question Section NEXT QUESTION ANSWER HINT

  46. (12) ANSWER: • Ethanethiol 2-mercaptoethanol • 1,2-Ethanedithiol Ethanedial • 2-mercaptoethanal • ANSWER: Ethanethiol < Ethanedial < 2-mercaptoethanal < 1,2-Ethanedithiol < 2-mercaptoethanol Question Section NEXT QUESTION ANSWER HELP

  47. (13) QUESTION: • The following molecule is the commonly known analgesic (Drug that • reduces pain) and antipyretic (Drug that reduces fever), • Acetaminophen (Tylenol™). Name all functional groups within the • Molecule. Question Section NEXT QUESTION ANSWER HINT

  48. (13) ANSWER: • ANSWER: hydroxyl, ketone, amine, benzene Amine Question Section Ketone Hydroxyl Benzene NEXT QUESTION ANSWER HELP

  49. CARBOXYLIC ACIDS are those molecules containing a carbon bonded to a hydroxyl and bonded to a carbonyl group simultaneously. When naming these molecules, ensure the addition of “oic” to the parent name followed by “acid”. Carboxylic Acids The Carboxylic Acid Functional Group NEXT SLIDE

  50. AMINES are the derivatives of Ammonias in which the hydrogen atoms (protons) have been replaced with alkyl groups (carbon) or aryl groups (benzene). As a parent chain the addition of the suffix “amine” is used. As a substituent, “aminois used. AMIDES are derivatives of carboxylic acids where the hydroxyl group has been substituted for a nitrogen group. Amides will often include structure that branch from the nitrogen group. The use of the suffix “amide” is used for as the parent chain. Amines and Amides The Amine Functional Group The Amide Functional Group NEXT SLIDE