Exam 3

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Exam 3
2012-06-25 06:51:45
UMD Chem

Organic Naming
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  1. IUPAC
    The International Union of Pure and Applied Chemistry 
  2. Naming Saturated Hydrocarbons
    • -prefixes:
    • meth, eth, prop, but, pent, hex, hept, oct, non, dec, undec, dodec

    • -suffixes:
    • • ane: single bonds
    • • ene: double bonds
    • • yne: triple bonds
  3. alkanes + cycloalkanes
    • • alkanes: simplest saturated hydrocarbons; have this general formula:
    • CnH2n+2

    • • cycloalkanes: cyclic saturated hydrocarbons; formula: CnH2n
  4. isomers
    chemical compounds that have the SAME molecular formulas but different structures
  5. Alkyl groups
    • • (represented by the symbol R) are common substituents
    • • are fragments of alkanes in which one H atom has been removed for the connection to the main chain (follow the formula (CnH2n+1)
    • - one carbon group = methyl
    • - two carbon group = ethyl
    • - three carbon group = propyl
  6. three classes of unsaturated hydrocarbons:
    1) alkenes/cycloalkenes [CnH2n]

    2) alkynes/cycloalkynes [CnH2n-2]

    3) aromatic hydrocarbons
  7. Alkenes
    • polyenes contain two or more double bonds per molecule

    • • the number of double bonds is indicated with suffixes:  
    • -adiene for two double bonds
    • -atriene for three double bonds

    • • position of the C=C bond(s) given the lowest number(s) 
    • possible
  8. Hybridization & Bonds in Hydrocarbons
  9. aromatic hydrocarbons
    refers to benzene, C6H6 & derivatives of benzene

    • • positions of the substituents on benzene rings are indicated by prefixes: 
    • -ortho (o-) for substituents on adjacent C atoms 
    • -meta (m-) for substituents on C atoms 1 and 3 
    • -para (p-) for substituents on C atoms 1 and 4 [parallel]
  10. o, m & p-xylene
    • xylene = benzene with 2 methyl groups (aka dimethylbenzene IUPAC)
    • o: 


  11. organic halides
    • hydrocarbon with a halogen atom in the place of a hydrogen atom
    • • are named alphabetically; bromo --> chloro --> flouro --> iodo
  12. alcohols & phenols
    derivatives of hydrocarbons in which one or more H atoms have been replaced by -OH groups

    • stem for the parent hydrocarbon + -ol suffix = systematic name for an alcohol

    • a numeric prefix indicates the position of the -OH group in alcohols with three or more C atoms

    • ex. can be 2-pentanol or 2-pentyl alcohol
  13. difference between phenol & phenyl
    • PHENOL: 
    • PHENYL: 
  14. alcohols can be classified into three classes:
    • 1) primary (1°) alcohols like ethanol have the -OH group attached to a C atom that has one bond to another C atom

    • 2) secondary (2°) alcohols have the –OH group attached to a C atom that has bonds to 2 other C atoms

    • 3) tertiary (3°) alcohols have the –OH group attached to a C atom that is bonded to 3 other C atoms
  15. polyhydric alcohols
    alcohols that contain more than one -OH group per molecule
  16. phenols
  17. ethers
    • 'derivatives' of water, but both H atoms are replaced with 2 R groups (alkyl or aryl groups)

    • -alkyl group (abbreviated R): functional group/side-chain that consists only of single-bonded carbon and hydrogen atoms (ex. methylor ethyl group)
    • -aryl group (R or R'):  any functional group/substituent derived from an aromatic ring (ex. phenyl, naphthyl, thienyl, indolyl)
  18. ether example: ethylmethyl ether
  19. functional groups
    specific groups of atoms or bonds within molecules that are responsible for the characteristic chemical reactions of those molecules

    • - the same functional group will undergo the same or similar chemical reactions regardless of the size of the molecule it is a part of
    • - its relative reactivity can be modified by nearby functional groups
  20. the functional group of both aldehydes & ketones is...
    carbonyl group (C == O)
  21. Ketones
    • • two organic groups bonded to a carbonyl group
    • • naming suffix: -one 
  22. examples of ketones: naming = stem for parent hydrocarbon + suffix one
    1) 3-hexanone (or ethyl propyl ketone)

    2) acetophenone (or methy phenyl keton) 
  23. Aldehydes
    • • can remember that aldehyde is the one with H as a substituent because it has an H in it [AldeHyde]

    • aldehydes have one H atom + one organic group bonded to a carbonyl group (exception: formaldehyde, which has 2 H groups bonded to a carbonyl)

    • naming suffix: -al
  24. examples of aldehydes:
    - common names are derived from the name of the acid w/ the same # of C's 
  25. Amines
    • derivatives of ammonia (NH3) in which one or more H atom has been replaced by an organic group

    • • there are 3 classes:
    • 1) primary ammine - central N is connected to 1 organic group & 2 H atoms 

    • 2) secondary - central N is connected to 2 organic groups & 1 H atom

    • 3) tertiary - central N is connected to 3 organic groups
  26. Carboxylic Acids
    • • has of carbonyl group + OH, aka a...
    • carboxyl functional group (CO2H): 

    • • general structure: caboxyl group + R group (alkyl/aryl)
    • • naming: names are derived from parent hydrocarbon; the final -e is dropped, & a -oic acid is added
  27. examples of Carboxylic Acids (simple):
    • 1) propanoic acid (or propionic acid)
    • 2) butanoic acid (or butyric acid)
  28. Carboxylic Acid Naming Rules (+ examples):
    • • substituent positions on carboxylic acid chains are indicated by number prefixes, just like for hydrocarbons
    • • however you BEGIN. COUNTING from the C atom in the carbonyl/carboxy group
    • • also the carbon atoms are labeled:
    • - 1st = alpha carbon (AFTER the carbonyl group)
    • - 2nd = beta carbon
    • -3rd = gamma carbon

    • example #1: 3-methylbutanoic acid (or B-methylbutanoic acid)
    • example #2: pentanoic acid (or γ-methylpentanoic acid)
  29. Dicarboxylic Acids
    contain two carboxyl groups per molecule (di)

    • 1) oxalic acid
    • 2) malonic acid
    • 3) succinic acid
  30. Aromatic Acids
    1) 2) 3)
    • • carboxylic acid chains whose R group is a benzene ring (or something similar)
    • • sometimes are named as derivatives of benzoic acid

    • 1) benzoic acid
    • 2) p-chlorobenzoic acid
    • 3) p-toluic acid (can you say p-methylbenzenoic acid?)
    • 4) phthalic acid: (ugh)
  31. Derivatives of Carboxylic Acids:
    acid anyhydride:

    acid chloride:


    • for compounds with more than one functional group; -highest priority group takes the suffix
    -all others taking the prefix
    -bonds: double and triple only take suffix (-en and -yn) & are used with other suffixes
    • 1) cations (highest priority; listed 1st in a compound name)
    • 2) carboxylic acids (C==O + -OH + R group)
    • 3) carboxylic acids [COOH] derivatives (ex. amides, esters, acid chlorides/anhydrides)
    • 4) aldehydes (R + C==O + H)
    • 5) ketones (R + C==O + R')
    • 6) phenols (benzene ring + -OH group)
    • 7) alcohols (hydrocarbon + -OH)
    • 8) amines (N≡RHH, R'R"H, or RR'R")
    • 9) ethers (like water; R1--O--R2)
    • 10) alkenes (double bond)
    • 11) alkynes (triple bond)
    • 12) organic halides (halogens: Cl-, Br-, I-)
    • 13) alkanes! (single bond)
  33. propyl
  34. 1-methylethyl (isopropyl, but that's not IUPAC)
  35. cyclopropyl (has priority over the other 2 types of propyl groups)
  36. Important to note in Priority Order:
    • (after carboxylic acids & their derivatives) aldehydes are named BEFORE ketones (A comes before K alphabetically)

    • special note for ketones: if their ==O group position isn't labeled with a number prefix, then it HAS to be at C #2... [if it were at carbon #1, the molecule would be an aldehyde]

    • then PHenols comes BEFORE alcohols

    • amines before ethers (again a before e)

    • double bonds have HIGHER naming priority than triple (get a lower number when their position is labeled!)

    • alkanes are last
  37. Isomers (organic)
    • isomers are molecules that have the same atom composition (ex. chemical formula) but DIFFERENT structures (molecular)
    • • there are 3 forms of isomerism
    • 1) conformational
    • 2) constitutional [structural]
    • 3) stereoisomerism [2 subtypes]
  38. conformational
    the differences in 3D structure come from rotation about a single (sigma) bonds; each arrangement is called a conformational isomer
  39. constitutional [structural]
    molecules have the same empirical formula but different atom-atom connections
  40. stereoisomerism [2]
    same atom-atom connections, but DIFFERENT spatial arrangements

    -geometric: only occur when there is a C=C double bond

    -optical: molecules that are non-superimposible mirror images of each other; called chiral molecules; pairs of chiral molecules are called enantiomers
    PROPYL GROUPS? I think...
  42. toluene
  43. Newman Projections
    • - eclipsed conformation: C–H bonds on adjacent carbon atoms are parallel and lie in the same plane 

    • - staggered conformation: hydrogen atoms are positioned as far from one another as possible; the staggered conformation is the most stable because electrostatic repulsion between the hydrogen atoms on adjacent carbons is minimized
  44. In the conversion of one constitutional isomer to another:
    at least one bond must be broken and reformed at a different position in the molecule 
  45. Geometric isomers can only occur when there is a:
    • - C=C double bond
    • - geometric isomers differ in placement of substituents in a rigid molecule; members of an isomeric pair are either cis or trans, with interconversion between the two forms requiring breaking and reforming one or more bonds
    • - structural differences causes them to have different physical and chemical properties and to exist as two distinct chemical compounds 
  46. Optical isomers are molecules with: 
    • non-superimposable mirror images
    • • such molecules are called CHIRAL 
    • • an achiral object is one that can be superimposed on its mirror image 
    • • pairs of chiral molecules are enantiomers
    • • Chiral molecules in solution can rotate the plane of plane polarized light 
  47. For sugars with more than one chiral center, the D or 
    L designation refers to the asymmetric carbon: 
    farthest from the aldehyde or keto group

    • -honestly, if the -OH is on the RIGHT, it's a D
    • -if the -HO is on the LEFT, it's an L
  48. Haworth projections 
    • represent cyclic sugars as having essentially planar rings, with the OH at the anomeric C1 extending either: 
    • •below the ring (alpha)  
    • •above the ring (beta)
  49. glycosidic bonds
    dehydration reaction to link 2 sugars, OH and OH join
  50. protein
    • central C is alpha carbon
  51. ligands
  52. ion-ion, versus coordination, where there's an exchange of ligands
  53. linkage isomers: 
    • if a ligand contains more than one atom with a free 
    • electron pair, the ligand may be bound to the central atom via the different atoms

    • bonding via N      nitro- 
    • bonding via O      nitrito- 

    • bonding via C      cyano- 
    • bonding via N      isocyano- 

    • bonding via S       thiocyanato- 
    • bonding via N      isothiocyanato-