Organic Chemistry

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Organic Chemistry
2013-02-22 14:24:35
Boston College NU 491

Organic Chemistry Review for Boston College Anesthesia Spring 1 semester
Show Answers:

  1. Organic molecules are comprised of what types of atoms? How are they bonded?
    Nonmetals: CARBON, hydrogen, nitrogen, oxygen, and halogens

    They are bonded together by covalent and polar bonds (not ionic).
  2. Why will carbon form 4 bonds?
    1s22s22p I   I      
  3. Why do organic mixtures have low boiling and melting points?
    The covalent bonds tend to mean that there are weaker intramolecular forces (than ionic compounds).
  4. Can functional groups be substituent groups?
  5. How are organic families categorized?
    Give some examples, please.
    They tend to be split up based on functional groups, which gives compounds their characteristic chemical behaviors.

    • Alkane
    • Alkene
    • Alkyne
    • Alcohol
    • Ether
    • Aromatics
    • Amine

    • Carbonyls:
    • Ester
    • Amide
    • Ketone
    • carboxylic acid
    • aldehyde
  6. Do organic compounds tend to be combustible?

  7. What is this molecule?
    Isopropyl (not propyl)

    Alkanes can become functional groups if they lose a hydrogen. The names change from -ane to -yl.

    This is called isopropyl because the hydrogen is removed from the middle carbon.
  8. What is a functional group?
    • It is a group of atoms that determine the characteristic properties of a compound because of its structure. (Based on its structure)
    • This determines how much the molecules will react with others and with receptors in order to affect a physiologic response.
    • Functional groups can be substituent groups.
  9. How are families of compounds determined?
    They are determined by their chemical properties and behaviors, which are determined by their functional groups.
  10. How does IUPAC want us to generally name compounds?

    • Prefix: what is attached to the carbon chain
    • Parent: longest chain of carbons
    • Suffix: family? (alkane, ether, etc.)

  11. What is this molecule? What family and type of anesthetic is it?
    • Cyclopropane
    • Cycloalkane, simplest carbon ring
    • Note at each carbon still makes 4 covalent bonds, but 2 of the bonds are to carbon and 2 are to hydrogens
    • Introduced in 1930s, volatile anesthetic
    • Low solubility, supported circulation

  12. What is the appropriate name for this molecule?
    1-bromo, 3-chloro cyclohexane

    When substituent groups are present, numbering starts with alphabetic priority and then proceeds so that the other second group will have the lowest number possible.
  13. What reactions do alkanes undergo?
    • Combustion
    • Halogenation
  14. Demonstrate combustion of alkanes:
  15. Properties of Alkanes:
    • Hydrocarbons - only single bonds; saturated
    • Low MW, low boiling point
    • Flammable, combustible
    • Nonpolar, insoluble in water, soluble in organic compounds
    • Less dense than water
    • Not very reactive
  16. What are the products of combustion?
    Water and CO2

    Water and CO if oxygen is insufficient.

  17. What is this molecule and how is it created?
    Trichloromethane, chloroform

    • It is created by the serial halogenation of methane.
    • CH4 + Cl2 --> CH3Cl + HCl
    • CH3Cl + Cl2 --> CH2Cl2 + HCl
    • CH2Cl2 + Cl2 --> CHCl3 + HCl

  18. Name this molecule. What family and type of anesthetic is it?
    • Halothane; 1-bromo, 1-chloro, 2,2,2 trifluroethane
    • Only alkane in current use a volatile anesthetic.
    • Introduced in 1956
    • Halogenated structure allowed it to not be flammable
  19. What does it mean when I say that alkanes are saturated?
    A saturated molecule is one in which each carbon is bonded to the maximum number of hydrogens.
  20. Why are alkenes and alkynes unsaturated?
    The double and triple bonds between the carbons mean that each carbon does NOT have the maximum possible number of hydrogens.
  21. What is an isomer?
    Compounds that have identical molecular formulas but different structure

    • Structural
    • Stereoisomers
  22. What is a constitutional/structural isomer?
    Same molecular formula but different connections/bonds among the individual atoms
  23. What is a stereoisomer?
    Identical molecular formulas and connections, but there are different arrangements in 3-dimensional space.

    • Optical
    • Geometric
    • Comformational

  24. How are these two molecules related?
    They have exactly the same molecular formulas, but they are structurally (and therefore) and chemically different.

    Structural/constitutional isomers!

  25. How are these molecules related?
    • Isoflurane and enflurane - both are ethers.
    • Structural (constitutional) isomers!

    • Very different properties: MAC, VP
    • Same oil:gas partition coefficient
  26. Which stereoisomers are classified based on how they react to plane polarized light?
    Optical isomers, enantiomers
  27. What is chiral?
    It means that things are not superimposable (think mirror images). This is a property that is used to characterized enantiomers.
  28. What is a racemic mixture?
    Equal mixture of enantiomers and results in being optically inactive (the optical isomers cancel each other out with opposing spins)
  29. Why are stereoisomers significant?
    Different enantiomers may have different properties or ADRs. They can vary in both pharmacokinetics and pharmacodynamics.

    Sometimes antagonize the effects of one another.

    Racemic mixtures may mean you have 2 different drugs, pharmacologically speaking. Sometimes dextrorotatory or levorotatory isomers may be isolated.
  30. What family organic molecules are prone to existing as geometric isomers?

  31. Cis or trans?

    Cis-trans isomerism does not apply when the functional groups are on the same carbon atom.

  32. Cis or trans?
    Cis! They are on the same side of the bond.

  33. Cis or trans?

    The methyl groups are on different carbon atoms on opposite sides of the double bond.
  34. What are some anesthetics that are supplied only as racemic mixtures of optical isomers?
    • Ketamine
    • Thiopental
    • Bupivicaine
    • Volatiles except sevoflurane
  35. Why is sevoflurane not considered to be an optical isomer?
    It is achiral.
  36. What are some anesthetics that are available as a single enantiomer of a racemic mixture?
    • Etomidate
    • Remifentanyl
    • Levobupivicaine
  37. What are some anesthetics that are structural isomers of each other?
    Enflurane and isoflurane
  38. What are some anesthetics that exhibit geometric cis-trans isomerism?

    (an enantiomer that does not cause histamine release like Atracurium did)
  39. What reactions do alkenes undergo?

    By what mechanism?
    • Additions
    • Eliminations
    • Substitutions
    • Rearrangements

    The double bonds between carbons break and then something happens!
  40. Name some examples of alkene addition reactions.
    • Hydrogenation
    • Hydrohalogenation
    • Hydration
    • Halogenation
  41. Describe Markovnikov's Rule.

    In which reactions does this rule apply?
    • The hydrogen goes to the carbon already bonded to the most hydrogens and the halogen goes to the other carbon. 
    • Hydrogens go to their friends!

    • Hydrohalogenation: yields an alkyl halide
    • Hydration: yields an alkane with hydroxy group (alcohol)
  42. Show the hydrogenation of ethene.
  43. What does the hydrogenation of an alkene yield?
  44. Show the halogenation of ethene.
  45. What does the halogenation of an alkene yield?
    Halogenated alkene
  46. Show the hydration of ethene.
  47. What does the hydration of an alkene yield?
    An alcohol
  48. Show the hydrohalogenation of ethene.
  49. What does the hydrohalogenation of an alkene yield?
    A halogenated alkane
  50. What is a polymer?
    A large molecule formed by the repetitive bonding together of many smaller molecules.
  51. What is a monomer?
    A small monomer that is used to prepare a polymer.
  52. What is a polymerization reaction?
    This occurs when a monomer is treated with a catalyst.
  53. What is the significance of methymethacrylate and how does it work?
    • This is a cement that is typically used in arthoplasty. 
    • It is a self polymerizing, space-filling mortar that transmits compressive loads. It achieves fixation by entering osseous spaces and engulfs trabeculae. 
    • It must be converted to a polymer at the right point in surgery.
    • Small sphere reaches 100C as a result of an exothermic reaction. This heat may cause necrosis and hypotension. (vasodilation? secondary to volatile monomer)
  54. List the properties of aromatic compounds.
    • Nonpolar
    • Water insoluble
    • Volatile
    • Flammable
    • Toxic - carcinogenic
    • Propofol contains a substituted beneze ring
  55. Ortho 1,2

  56. Meta 1,3

  57. Para 1.4


  58. What is this molecule?
    Benzene ring (Ar; C6H6); aromatic compound. Is NOT a cycloalkane because of its double bonds.

  59. What is this molecule?
    • Phenyl group
    • C6H5-
    • It is a functional group when the benzene ring is the substituent.
  60. -OH
    Hydroxyl group
  61. R-OH
  62. Can you find a hydroxyl group on an alkene?
    No. Alcohols are compounds that have hydroxyl groups bound to a saturated, alkane-like carbon atom.

  63. What is this molecule?

    (not cyclohexanol)
  64. Name some properties of alcohols:
    • Organic derivatives of water
    • More polar than hydrocarbons such as alkanes because of the hydrogen bonding caused by the -OH group. (lone pairs on oxygen atom)
  65. Primary alcohol
  66. Secondary alcohol
  67. Tertiary alcohol
  68. How will what determines the solubility of an alcohol?
    • The length of the carbon chain. 
    • The more carbons, more organic, less water soluble.
    • Fewer carbons means the influence of -OH group is greater.
  69. What reactions do alcohols typically undergo?
    • Dehydration
    • Oxidation
  70. Demonstrate the dehydration of ethanol.
    • The H and OH must come from separate carbons.
  71. What does the dehydration of an alcohol yield?
    Alkene and water
  72. What does the oxidation of an alcohol yield?
    • Increased number of carbon-oxygen bonds
    • Decreased number of carbon-hydrogen bonds
    • --> Carbonyl compound (aldehyde or ketone)
  73. Demonstrate the oxidation of a primary alcohol.
  74. What does the oxidation of a primary alcohol yield?
    Water and an Aldehyde
  75. Demonstrate the oxidation of a secondary alcohol.
  76. What does the oxidation of a secondary alcohol yield?
    Water and a Ketone
  77. Demonstrate the oxidation of a tertiary alcohol.
    • There is not enough hydrogen available to attach to -OH make the H2O!
  78. How is alcohol metabolized?
    • In a 2-step oxidation process:
    • Step 1 --> aldehyde (ethanol is a primary alcohol)
    • Step 2 --> acetic acid (carboxylic acid)
  79. How will ethyl alcohol ingestion affect anesthesia?
    • CNS depression
    • Acute ingestion decreases anesthetic requirements
    • Chronic use/abuse induces the cytochrome P-450 system and increases anesthetic requirements due to accelerated metabolism.
  80. Is phenol a polar compound?
    Yes, the lone pair on the oxygen will encourage hydrogen bond formation.
  81. Why is phenol no longer utilized?
    It was originally used as a topical antiseptic but it turned out to be toxic.
  82. R-O-R'
  83. How are ethers named?
    Name the R and R' groups and add "ether."
  84. R-O-
    Alkoxyl group, which is ether as a substituent

  85. CH3O-
    methoxy group (substituent on methoxyflurane)
  86. What is ether like as an anesthetic?
    • Quick acting
    • Very effective
    • Long recovery time (high solubility)
    • Pungent; unpleasant induction
    • High incidence of nausea and vomiting
    • Highly flammable liquid vapor forms explosive mixtures with air
  87. Which volatile anesthetics are considered to be halogenated ethyl methyl ethers?
    Enflurane, isoflurane, methoxyflurane, and desflurane

    NOT sevoflurane (methylisopropyl ether)

  88. Name this molecule. What family and type of anesthetic is it?
    Desflurane; ether; volatile

  89. Name this molecule. What family and type of anesthetic is it?
    Sevoflurane (methylisopropyl ether); ether; volatile

  90. Name this molecule. What family and type of anesthetic is it?
    Isoflurane; ether; volatile

  91. Name this molecule. What family and type of anesthetic is it?
    Enflurane; ether; volatile

  92. Name this molecule. What family and type of anesthetic is it?
    Methoxyflurane; ether; volatile
  93. R-N-H2
  94. Why will nitrogen form 3 covalent bonds?
    1s22s22p I   I   I  
  95. Is NH3 an organic compound?
    No, there is no carbon.
  96. Why is the lone pair in ammonia (NH3) significant?
    • It permits a fourth group to bond to the nitrogen. 
    • It may be R group or hydrogen (NH4+)

  97. What is this and why is it significant?
    Quaternary ammonium compound (cation)

    This is important in anesthesia because this is a key component to nondepolarizing muscle relaxants. The positive charge limits the distribution to ECF so there are no CNS effects. It goes to NMJ, but not CNS thanks to the charge.

  98. What is this molecule?
    Primary amine

  99. What is this molecule?
    Secondary amine

  100. What is this molecule?
    Tertiary amine
  101. List some properties of amines.
    • Weak base (tends to accept a hydrogen ion from acids)
    • Can form hydrogen bonds because of nitrogen's lone pair
    • Boiling point is higher than alkanes because of hydrogen bonding (stronger IMF), but lower than that of alcohols
    • Volatile amines have a strong odor because of the degradation of proteins?
    • Simpler amines are water soluble (hydrogen bonding)
    • Toxic to eat
  102. Why will atropine cause CNS effects (mad as a hatter) and not glycopyrollate?
    Atropine is a tertiary amine, and glycopyrollate is a quaternary amine. So the former crosses BBB and the latter cannot.

  103. Tell me about this structure.
    3,4 dihydroxy benzene + amine = the basic structure of a catecholamine

    Start "lettering" the substitutions at the carbons (alpha, beta, gamma) from the functional group.

  104. What is this molecule?

  105. What is this molecule?

  106. What is this molecule?

  107. What is this molecule?

  108. What is this molecule?

  109. What is this molecule?
  110. What is the difference between an ester and an ether?
    Ester has C=O and ether does not.
  111. What is the difference between an amide and amine?
    Amide has C=O, and amine does not.
  112. Give some examples of carbonyl compounds.
    • Esters
    • Amides
    • Carboxylic acid
    • Aldehyde
    • Ketone
  113. What is the defining characteristic of a carbonyl compound?

  114. Identify this functional group.

  115. Identify this functional group.

  116. Identify this functional group.

  117. Identify this functional group.
    Carboxylic acid

  118. Identify this functional group.
  119. Are organic acids weaker or stronger than inorganic acids?

  120. What is this molecule?
    Carbonic acid (H2CO3)
  121. How do you name carboxylic acid?
    Replace the final "e" of alkane with "-oic acid"
    What is this molecule?
    • GABA
    • gamma-aminobutyric acid

  123. Name this molecule.
    Alpha hydroxy acid

  124. What is this group and how does naming work?
    Acyl group. 

    • This is what remains when carboxylic acid loses -OH. Replace the "-ic" and add "-oyl" to the end of the acid name.
    • EXCEPTION: acetic acid/acetyl group
  125. What are the reactions that carboxylic acids undergo?
    • Esterification
    • Amide formation
  126. Demonstrate esterification:
    • Carboxylic acid + alcohol = ester + water
  127. Demonstrate amide formation:
    • Unsubstituted amides: carboxylic acid + ammonia = amide + water

  128. What is this?
  129. How are esters metabolized?
    via ester hydrolysis, NOT the liver (CYP-450)
  130. How are amides metabolized?
    via the liver CYP-450
  131. Why are esters and amides significant for anesthesia?
    They are used in local anesthetics.
  132. What family of local anesthetics has a greater potential for allergic reactions? Why?

    Paraminobenzoic acid is a metabolite that is a common allergen.

  133. What is this molecule? What is its significance?
    • para-Amino benzoic acid
    • (Acid group is functional group, so that is on carbon 1, amine group is then carbon 4 --> para groups on benzene ring)

    It is the metabolite of an ester that often causes allergic reaction.
  134. What is the preservative that many may be allergic to in an amide?
    Methyl paraben
  135. Give some anesthesia examples of alkanes.
    • cyclopropane
    • halothane
    • chloroform
  136. Give some anesthesia examples of alkyl halides.
    • halothane
    • chloroform (general anesthetic)
    • Ethyl chloride (topical anesthetic)
  137. Give some anesthesia examples of alcohols.
  138. Give some anesthesia examples of amines.
    • Ketamine
    • Neurotransmitters
    • paralytics (block Ach at NMJ)
    • acetylcholine (atropine and glycopyrollate block it)
  139. Give some anesthesia examples of ethers.
    • NOT halothane
    • desflurane
    • enflurane
    • isoflurane
    • sevoflurane
  140. Give some anesthesia examples of esters.
    Local anesthetics such as procaine/novocaine, tetracaine, chloroprocaine.
  141. Give some anesthesia examples of amides.
    • Local anesthetics such as:
    • (They have 2 "i"s in the names)

    • lidocaine
    • bupivicaine
    • mepivicaine

  142. Name this molecule.

  143. Name this molecule.

  144. Name this molecule.

  145. What is this molecule?
    Ethyl alcohol as exhibited by the 2-carbon chain and hydroxyl group.

  146. Name this molecule. What family and type of anesthetic is it?
    Dimethyl ether; volatile
  147. Diethyl ether
  148. Dimethyl ether
  149. Ethyl methyl ether

  150. Identify this molecule.
    • Propofol
    • 2,6 diisopropylphenol
  151. Name 2 anesthetics that are structural isomers of each other.
    Enflurane and isoflurane
  152. Name an anesthetic that is a geometric isomer.
  153. Name 2 anesthetics that exists as a racemic mixture of enantiomers.
    • Bupivicaine
    • Ketamine
    • Thiopental
  154. Name 2 anesthetics that exist as a single enantiomer.
    • Etomidate
    • Levobupivicaine