C341 SP2024 Week 2 Chapter 2 KEY

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Indiana University, Bloomington *

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341

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Chemistry

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Feb 20, 2024

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pdf

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Uploaded by SuperDangerPrairieDog41

C341 Chapter 2 Page 1 of 5 1.) Intermolecular forces . Many esters have distinctive fruit ‐ like odors, and many occur naturally in the essential oils of plants. This has also led to their common use in artificial flavorings and fragrances which aim to mimic those odors. Below are two molecules that lend themselves to the cherry fruit flavor. Indicate the intermolecular forces exhibited by each molecule in a pure sample. Choices are London forces ( LF ), dipole ‐ dipole ( DD ), hydrogen bonding ( HB ). Use acronyms for your answers. Then determine if the molecules below are water soluble ( WS ) or fat soluble ( FS ). a.) Provide the molecular formula for the molecules. b.) List the intermolecular forces exhibited by each molecule in a pure sample. Choices are London forces ( LF ), dipole ‐ dipole ( DD ), hydrogen bonding ( HB ). Use acronyms provided for your answers. c.) Predict if fat soluble ( FS ) or water soluble ( WS )? Use acronyms provided for your answers. 2.) Constitutional isomers . For the following compound, identify its molecular formula and then draw several constitutional isomers. Cly Hey02 6541003 LF DD LF DD HB FS WS 6541003 OH 5 MANY no on the Howl on I CE 85 0H what it oct 1 of homat

C341 Chapter 2 Page 2 of 5 3.) Functional groups . Identify and circle all the different functional groups in these two compounds. If you can be descriptive, such as using 1 o , 2 o , etc., than do so. 4.) Provide line drawings for the following functional groups containing five carbons (and exactly five carbons). Try drawing a couple different constitutional isomers for each. 2 o alcohol ketone ester amide 1 o amine ether aldehyde 3 o alkyl halide carboxylic acid arene zoam.me 20 add 30 amide ether arene ester cabad Lamine 20 alcohol arene ketone 20 amine ester aside alkene HOW or NF MNH not WEH out

C341 Chapter 2 Page 3 of 5 5.) Conjugation. Molecule A Molecule B Draw orbital drawings of the pi ‐ orbitals for the molecules above. Are the molecules above conjugated? Briefly explain. If so, how many p ‐ electrons are in conjugation? Molecule C Molecule D Draw orbital drawings of the pi ‐ orbitals for the molecules above. Are the molecules above conjugated? Briefly explain. If so, how many p ‐ electrons are in conjugation? 88k 8T Molecule A conjugated 4 it e on 4 consecutive atoms with 4 overlapping p orbitals Molecule B not conjugated 8T 8 6 it e 5 p orbitals 4 it e 5 p orbitals Both are conjugated through the 5 Porbitals on 5 adjacent atoms

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C341 Chapter 2 Page 4 of 5 6.) Conjugation . Fill in the missing lone pairs below. Molecule E Molecule F Draw orbital drawings of the pi ‐ orbitals for the molecules above. Are the molecules above conjugated? Briefly explain. If so, how many p ‐ electrons are in conjugation? 7.) Conjugation . Carotenoids are yellow, orange, and red organic pigments that are produced by plants and algae, as well as several bacteria, and fungi. Carotenoids give the characteristic color to pumpkins, carrots, parsnips, corn, tomatoes, canaries, flamingos, salmon, lobster, shrimp, many birds, and daffodils. One 2013 study demonstrated that regular ingestion of lutein ( naturally occurring carotenoid , structure below ) as a dietary supplement formulation containing lutein reduced progression of age ‐ related macular degeneration (AMD) by 25%. Orally consumed supplements are one of the fastest growing areas of the US$2 billion carotenoid market! The conjugated π‐ system in lutein above is composed of ______ p ‐ orbitals containing ________ delocalized π‐ electrons. ( Fill in the blanks appropriately.) 88 8 0 0 6 IT e 5 p orbitals 2 IT e isolated Molecule E is conjugated with 6 it e spread over 5 p orbitals Molecule F not conjugated 20 20

C341 Chapter 2 Page 5 of 5 8.) Localized and delocalized electrons . Localized lone pairs are NOT in conjugation, whereas delocalized lone pairs are in conjugation with pi ‐ electrons. Localized lone pairs live in hybrid orbitals and do not participate in resonance. Delocalized lone pairs live in p ‐ orbitals and participate in conjugation and resonance. For each compound below, fill in the missing lone pairs, indicate whether each lone pair is a localized lone pair ( LLP ) or a delocalized lone pair ( DLP ), the orbital in which the lone pairs reside, the hybridization of the atom, it’s shape and its ideal bond angle. Example: Argiotoxin is a low molecular weight neurotoxin released in several spider venoms. Acylpolyamines help paralyze invertebrate victims by blocking ion channels that are activated by glutamate, but it can also be effective against vertebrate nervous systems in large enough doses. Fill in the following table below based on the structure of Argiotoxin provided above. (If there are multiple LP with differing descriptions, list both with the correct orbital descriptions.) How many lone pairs? Types of lone pairs? Hybridization of atom ? Shape of central atom? Bond angle? Atom A Atom B Atom C Atom D Atom E Atom F a 1 DLP P sp trigonal planar 120 1 LLP sp sp bent 2120 1 LLP Sp3 sp trigonalpyramidal 2109.50 none sp's tetrahedral 109.50 none Sp trigonal planar 1200 2 LLP sp DLP p sp trigonal planar 1200