LT2 - Nomenclature

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Dec 6, 2023

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CHEM 210B Day ____ Date: ___/___/2023 LT2: Nomenclature Page 1 LT2: O RGANIC N OMENCLATURE A working knowledge of organic compound naming can be extremely useful – whether while taking CHEM 213 (the lab course) or deciphering ingredients in products you use or consume. After the class session, you will have learned the systematic method of naming organic compounds of selected families. This method is the IUPAC system . Learning Objectives By the end of this worksheet you will be able to: 2.1 Draw structures of organic compounds from the IUPAC nam 2.2 Use the IUPAC rules to name an organic compound. Reading and Video Connections • Nomenclature: Ch. 2: 2.3-4a (alkanes and cycloalkanes); Ch. 5: 5.2 (alkenes); Ch. 7: 7.2 (alkynes), Ch. 8: 8.1-2 (alkyl halides), Ch. 10: 10.1 (alcohols), Ch. 11: 11.2 (ethers), Ch. 16: 16.2 (aldehydes and ketones), Ch. 17: 17.2 (carboxylic acids), Ch. 18: 18.1 (amides, esters) Key Terms (come back to define these) • IUPAC nomenclature

CHEM 210B Day ____ Date: ___/___/2023 LT2: Nomenclature Page 2 Functional Groups in a Flash! 1. Name the functional groups / families depicted below! 2. Now apply those ‘definitions’ to actual organic molecules – some are monofunctional and others are multifunctional! O N H O O O NH 2 HO O O H O OH

CHEM 210B Day ____ Date: ___/___/2023 LT2: Nomenclature Page 3 Is the systematic method of naming organic compounds similar from family to family? The format of an organic compound’s IUPAC name is: substituent - parent - suffix Substituents: groups bonded to the parent chain Parent chain : the longest, continuous carbon chai n Suffix: the highest priority family 1. When learning to name organic compounds, it’s best to start out by drawing the compound from its IUPAC name. Try it with your team! 5-ethyl-2-methyl hept ane alkyl substituents # Cs substituents 1 methyl 2 ethyl 3 propyl 4 butyl Suffix Family Suffix alkane -ane alkene -ene alkyne -yne amine -amine alcohol -ol ketone -one aldehyde -al amide -amide ester -oate carboxylic acid -oic acid Parent chain # Cs parent name 1 meth 2 eth 3 prop 4 but 5 pent 6 hex 7 hept 8 oct 9 non 10 dec

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CHEM 210B Day ____ Date: ___/___/2023 LT2: Nomenclature Page 4 a. What information do the numbers within the name communicate? Is there another way to number the substituents? b. What can you tell about the order of the substituents in the name? Some substituents have their own branching and have common names for simplicity. The arrow indicates the point of attachment to the parent chain. We will only cover these common names. The names of the substituents above come from the substitution of the carbon atom at the point of attachment. a. A primary carbon has carbon groups. b. A secondary carbon has carbon groups. c. A tertiary carbon has carbon groups. d. A quaternary carbon has carbon groups. propyl isopropyl isobutyl tert- butyl sec- butyl butyl phenyl

CHEM 210B Day ____ Date: ___/___/2023 LT2: Nomenclature Page 5 The substitutions above translate to other functional groups such as alcohols and alkyl halides. The different types have different reactivities as we will see in a couple weeks and it is important to be able to classify them in this way. 2. Identify the substitution of the indicated atoms in the structure below: 3. Draw the structures of the following compounds: a. 1-phenylpentan-2-ol b. 3- tert -butylcyclohexanone c. Try these at home: 2- sec- butylcyclobutanamine and 2-ethyl-3-isopropylnonanoic acid OH Br

CHEM 210B Day ____ Date: ___/___/2023 LT2: Nomenclature Page 6 If two or more of the following families are present in an organic compound, you must identify the highest priority family as the suffix . If a family is not the highest priority, then it is a substituent . This table will guide you correctly each time: - If a halogen is present, it will be a substituent; e.g. bromo, chloro . - If an alkene or alkyne is present in a compound with any of the above families, then replace “an” with “ en ” (alkene)- or “ yn ” (alkyne) is included in the suffix , not as a substituent. 4. Dissect the name – tell what each part communicates. Then, draw the structure! 6-hydroxyhex-4-en-3-one Nomenclature family priority Suffix name As substituent highest CO 2 H carboxylic acid -anoic acid n/a CO 2 R ester -anoate n/a CONR 2 amide -anamide n/a CHO aldehyde -anal -oxo- CRO ketone -anone -oxo- OH alcohol -anol -hydroxy- SH thiol -anthiol -mercapto- NR 2 amine -anamine -amino- alkene -ene n/a alkyne -yne n/a lowest ether/sulfide/halogen/alkyl n/a alkoxy/alkylthio/halo/alkyl

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CHEM 210B Day ____ Date: ___/___/2023 LT2: Nomenclature Page 7 5. Spend ~5 or so minutes with your team to practice your name-to-structure skills by drawing the skeletal structures of the following compounds. - Hyphens – separate numbers from letters, e.g. 3-methyl , Commas , separate numbers from numbers (locants); e.g. 2,3- a. 4-methylhept-5-ynal b. 2-amino-3,4-dimethylpentanoic acid i. What is “di” used for here? c. 3,3-dimethyloctane i. Why are there two 3s?

CHEM 210B Day ____ Date: ___/___/2023 LT2: Nomenclature Page 8 Amines have some additional considerations for their IUPAC names. An amine group may have multiple carbon substituents bonded to the nitrogen. In order to designate those carbon groups from substituents bonded to the parent chain, a “ N ” is used as the location marker (the same applies to amides !). 6. Try to draw this amine from its IUPAC name: a. 3-isopropyl-4, N -dimethyloctan-1-amine b. A primary amine has carbon groups on N. c. A secondary amine has carbon groups on N. d. A tertiary amine has carbon groups on N. Writing IUPAC names from skeletal structures. IUPAC rules for naming: 1. Identify the principle functional group. Consider all functional groups according to the priority table on page 5. This gives you the suffix . 2. Find the longest continuous carbon chain that contains the highest priority functional group (and the most branching if more than one possibility); this is the parent chain . 3. Number the parent chain such that the highest priority family has the lowest number possible . If there is a “tie” when assigning a locant to other substituents, the lower number should be given to the one that comes first alphabetically. 4. List the substituents (with number locations) alphabetically (now, you’re starting to write the IUPAC name!). For secondary & tertiary amines/amides: use “ N -“ in front of the substituent rather than a number. Do NOT alphabetize prefixes tert -, sec -, di-, tri-, etc. 5. Then, follow with the parent chain with the highest priority family’s suffix , including double and triple bonds if present since these bonds are part of the parent chain, not a substituent. Now you have substituents - parent - suffix – the IUPAC name!

CHEM 210B Day ____ Date: ___/___/2023 LT2: Nomenclature Page 9 7. Take a few minutes to write the IUPAC name for the following skeletal structures: a. b. Try these –amino acids with multiple functional groups! c. A tricky one! What rule do you use to determine the numbering? S OH O NH 2 methionine HO O OH NH 2 glutamic acid O SH

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