Biochem-Org_Chem

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PicOlio
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117976
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Biochem-Org_Chem
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2011-11-26 16:36:54
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Organic chemistry
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Misc Review Intro to Organic and Biochemistry
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  1. Organic Chemistry
    The chemistry of the compounds of Carbon, as well as Hydrogen, Oxygen, Nitrogen, Sulfur, Phosphorus, and a Halogen (fluorine, chlorine, bromine, iodine)
  2. Organic Properties
    • Bonding is almost entirely covalent
    • Many are gases, liquids, or solids w/ low melting points
    • Most are insoluable in water
    • Most are soluable in organic solvents
    • Almost all burn and decompose
    • Reactions are usually slow
  3. Bond angles and Geometries
    • Tetrahedral: 109.5 degrees - Single bond
    • Trigonal Planar: 120 degrees - Double bond
    • Linear Molecule: 180 degrees - Triple Bond
  4. Functional Group
    An atom or group of atoms within a molecule that show a characteristic set of predictable physical and chemical behaviors.
  5. Define Hydrocarbon (saturated and unsaturated)
    • Hydrocarbon: A compound that contains only carbon and hydrogen atoms.
    • Saturated: Only Carbon-Carbon single bonds (alkanes)
    • Unsaturated: A hydrocarbon that contains one or more carbon-carbon double bonds (alkenes), triple bonds (alkynes), or benzene rings (arenes).
  6. Constitutional Isomers
    Compounds that have the same molecular formula but different structural formulas.
  7. Iso-
    Iso- indicates that one end of an otherwise unbranched chain terminates in a (CH3)2CH- group

    • Example: Isopropanol
  8. Prefixes: Counting Carbons to 20
    • 1. Meth-
    • 2. Eth-
    • 3. Prop-
    • 4. But-
    • 5. Pent-
    • 6. Hex-
    • 7. Hept-
    • 8. Oct-
    • 9. Non-
    • 10. Dec-
    • 11. Undec-
    • 12. Dodec-
    • 13. Tridec-
    • 14. Tetradec-
    • 15. Pentadec-
    • 16. Hexadec-
    • 17. Heptadec-
    • 18. Octadec-
    • 19. Nonadec-
    • 20. Eicos-
  9. Stereoisomers
    Isomers that have the same connectivity of their atoms but a different orientation of their atoms in space
  10. For any group of alkane constitutional isomers, the least branched isomer generally has the ____ boiling point and the most branched isomer generally has the ___ boiling point.
    For any group of alkane constitutional isomers, the least branched isomer generally has the highest boiling point and the most branched isomer generally has the lowest boiling point.
  11. Combustion
    Alkane + O2 ---> CO2 + H2O + Heat
  12. Markovnikov's Rule
    "The Rich Get Richer" meaning hydrogen bonds to the doubly bonded carbon that has the greater number of hydrogens bonded to it; the halogen or oxygen bonds to the other carbon.
  13. Regioselective Reaction
    A reaction in which one direction of bond forming or bond breaking occurs in preference to all other directions.
  14. Reaction Mechanism
    A step-by-step description of how a chemical reaction occurs.
  15. Arene
    Term used to describe aromatic hydrocarbons (a compound containing one or more benzene-like rings)
  16. An aldehyde can be oxidized to
    An aldehyde can be oxidized to a carboxylic acid
  17. A ketone can be reduced to
    A ketone can be reduced to a secondary alcohol.
  18. An aldehyde can be reduced to
    An aldehyde can be reduced to a primary alcohol.
  19. A primary alcohol can be oxidized to
    A primary alcohol can be oxidized to an aldehyde then a carboxylic acid
  20. Addition of an alcohol to an aldehyde produces
    Addition of an alcohol to an aldehyde produces a hemiacetal
  21. An ester is formed by the reaction between a carboxylic acid and
    An ester is formed by the reaction between a carboxylic acid and alcohol
  22. What molecules are involved in chemical communications?
    Cell-to-cell communications are carried out by three kinds of molecules

    • 1. Receptors: protein molecules embedded in the membranes of cells
    • 2. Chemical messengers, or ligands: interact with receptors
    • 3. Secondary messengers: carry and amplify the signals from the receptor to inside the cell
  23. An aldehyde can be oxidized to a(an)

    A. ketone
    B. ester
    C. alcohol
    D. carboxylic acid
    D. carboxylic acid

    (this multiple choice question has been scrambled)
  24. A ketone can be reduced to a(an)

    A. aldehyde
    B. alcohol
    C. carboxylic acid
    D. amide
    B. A secondary alcohol
    (this multiple choice question has been scrambled)
  25. A primary alcohol can be oxidized to a(an)

    A. ester
    B. ether
    C. aldehyde
    D. ketone
    C. Aldehyde and then a carboxylic acid
    (this multiple choice question has been scrambled)
  26. A secondary alcohol can be oxidized to a(an)

    A. aldehyde
    B. ketone
    C. amide
    D. carboxylic acid
    B. ketone
    (this multiple choice question has been scrambled)
  27. A primary alcohol can be oxidized to a(an)

    A. carboxylic acid
    B. ketone
    C. ester
    D. amine
    A. aldehyde and then a carboxylic acid
    (this multiple choice question has been scrambled)
  28. An aldehyde can be reduced to a(an)

    A. ketone
    B. ether
    C. alcohol
    D. carboxylic acid
    C. alcohol

    Aldehydes are reduced to primary alcohols
    (this multiple choice question has been scrambled)
  29. Which reaction involves cleavage of a carbon-carbon bond?

    A. reduction
    B. saponification
    C. dehydration
    D. decarboxylation
    A. reduction
    (this multiple choice question has been scrambled)
  30. Which of the following is a primary alcohol?

    A. methyl acetate
    B. 1-hexanol
    C. propanal
    D. 2-pentanone
    B. 1-hexanol
    (this multiple choice question has been scrambled)
  31. Which of the following is a secondary alcohol?

    A. 3-hexanone
    B. 2-heptanol
    C. 2-methyl-2-propanol
    D. 1-pentanol
    B. 2-heptanol
    (this multiple choice question has been scrambled)
  32. Which of the following is an ester?

    A. ethyl acetate
    B. isopropanol
    C. 2-hexanone
    D. heptanal
    A. ethyl acetate

    (this multiple choice question has been scrambled)
  33. Which term best describes the relationship between D-fructose and L-fructose?

    A. constitutional isomers
    B. epimers
    C. diastereomers
    D. enantiomers
    D. enantiomers

    To say that D- and L- are enantiomers means that they are nonsuperposable mirror images.
    (this multiple choice question has been scrambled)
  34. Which of the following has the highest boiling point?

    A. 1-butanol
    B. butanoic acid
    C. 2-butanone
    D. 1-aminobutane
    B. butanoic acid

    Carboxylic acids have high boiling points
    (this multiple choice question has been scrambled)
  35. Which compound does not exhibit hydrogen bonding?

    A. CH3COCH2CH3
    B. CH3NHCH2CH3
    C. CH3CH2COOH
    D. CH3CHOHCH3
    A. CH3COCH2CH3

    Only very weak dipole-dipole interactions
    (this multiple choice question has been scrambled)
  36. Which substance has an ester functional group?

    A. shortening
    B. honey
    C. vinegar
    D. sugar
    A. shortening

    There are ester bonds in fatty acids. Vinegar has carboxylic acid, sugar and honey have ether bonds
    (this multiple choice question has been scrambled)
  37. Which substance is chiral?

    A. 2-pentanol
    B. 2-hexanone
    C. 3-pentanol
    D. 1-hexanol
    A. 2-pentanol
    (this multiple choice question has been scrambled)
  38. Of those given, which substance is most water soluble?

    A. alkene
    B. alkyl halide
    C. alcohol
    D. alkane
    C. alcohol
    (this multiple choice question has been scrambled)
  39. Addition of an alcohol to an aldehyde produces a(an)

    A. hemiacetal
    B. amide
    C. ether
    D. ester
    A. hemiacetal

    Hemiacetals react further w/ alcohols to form acetals plus water.
    (this multiple choice question has been scrambled)
  40. Which class of products is characterized by four fused rings?

    A. alkaloids
    B. terpenes
    C. steroids
    D. tetrapeptides
    C. steroids
    (this multiple choice question has been scrambled)
  41. Purifying a liquid through vaporization followed by condensation is known as

    A. sublimation
    B. distillation
    C. filtration
    D. recrystallization
    B. distillation
    (this multiple choice question has been scrambled)
  42. Which base is found in RNA but not DNA

    A. guanine
    B. uracil
    C. cytosine
    D. adenine
    B. uracil
    (this multiple choice question has been scrambled)
  43. Which one of the following is not a component of nucleotides?

    A. phosphate
    B. lipid
    C. monosaccharide
    D. pyrimidine
    B. lipid

    A nucleotide = Base + sugar + phosphate
    (this multiple choice question has been scrambled)
  44. An ester is formed by the reaction between a carboxylic acid and

    A. amine
    B. ether
    C. alcohol
    D. ketone
    C. alcohol

    Fischer esterification: -OH from the acid and -H from the alcohol to remove the H2O and "squish together" the remaining ester.
    (this multiple choice question has been scrambled)
  45. The substances in the duodenum that emulsify fat globules into tiny droplets are

    A. phospholipids
    B. bile salts
    C. lipoproteins
    D. micelles
    B. bile salts

    Because they are eliminated in the feces, bile salts remove excess cholesterol in two ways 1) they are themselves breakdown products of cholesterol and 2) they solubilize deposited cholesterol in the form of bile salt-cholesterol particles -- micelles
    (this multiple choice question has been scrambled)
  46. Energy gained in the oxidation of food is stored in the form of

    A. ATP
    B. AMP
    C. ADP
    D. GMP
    A. ATP
    (this multiple choice question has been scrambled)
  47. The removal of excess blood glucose is facilitated by this hormone through enhancing cellular uptake and inducing storage pathways.

    A. adrenalin
    B. insulin
    C. testosterone
    D. estrogen
    B. insulin
    (this multiple choice question has been scrambled)
  48. What type of bonds hold together the two strands of DNA?

    A. polar covalent
    B. covalent
    C. ionic
    D. hydrogen
    D. hydrogen
    (this multiple choice question has been scrambled)
  49. The arrangement of the two DNA strands in relation to each other is

    A. parallel
    B. anti-parallel
    C. perpendicular
    D. tetrahedral
    B. anti-parallel
    (this multiple choice question has been scrambled)
  50. The backbone of DNA consists of _____.
    Adenine, thymine, guanine, and cytosine

    A-T and G-C
  51. What is the primary function of mRNA?

    A. Combines with proteins to form ribosomes, the site of protein synthesis
    B. Affects gene expression; important in growth and development
    C. Affects gene expression; used by scientists to knock out a gene being studied.
    D. Directs amino acid sequence of proteins
    E. Processes initial mRNA to its mature form in eukaryotes
    F. Transports amino acids to site of protein synthesis
    D. Directs amino acid sequence of proteins

    Messenger RNA
    (this multiple choice question has been scrambled)
  52. What is the primary function of tRNA?

    A. Affects gene expression; used by scientists to knock out a gene being studied.
    B. Combines with proteins to form ribosomes, the site of protein synthesis
    C. Processes initial mRNA to its mature form in eukaryotes
    D. Directs amino acid sequence of proteins
    E. Affects gene expression; important in growth and development
    F. Transports amino acids to site of protein synthesis
    F. Transports amino acids to site of protein synthesis

    Transfer RNA
    (this multiple choice question has been scrambled)
  53. What is the primary function of rRNA?

    A. Combines with proteins to form ribosomes, the site of protein synthesis
    B. Processes initial mRNA to its mature form in eukaryotes
    C. Directs amino acid sequence of proteins
    D. Transports amino acids to site of protein synthesis
    E. Affects gene expression; used by scientists to knock out a gene being studied.
    F. Affects gene expression; important in growth and development
    A. Combines with proteins to form ribosomes, the site of protein synthesis

    Ribosomal RNA
    (this multiple choice question has been scrambled)
  54. Which is a stronger base?

    An aliphatic amine or an aromatic amine?
    Aliphatic amines are a stronger base than aromatic amines.

    Aromatic amines are weaker bases than aliphatic.
  55. ethane + O2 -yields-> _____ + _____
    2CH3-CH3 + 7O2 --yields--> 4CO2 + 6H2O + Heat

    An alkane plus oxidation is combustion and it results in Carbondioxide plus water plus heat.
  56. The following compounds have comparable molecular weights. Which one has the highest boiling point?

    A. 2-propanol
    B. butane
    C. 2-methylpropane
    D. 2-propanamine
    A. 2-propanol
    (this multiple choice question has been scrambled)
  57. Which statement about amines is incorrect?

    A. Amines are polar compounds
    B. Aromatic amines in general are weaker bases than aliphatic amines.
    C. Generally, aqueous solutions of amines are basic.
    D. Aliphatic amines are stronger bases than inorganic bases such as NaOH and KOH
    D. Aliphatic amines are stronger bases than inorganic bases such as NaOH and KOH

    Aromatic amines are weaker bases than aliphatic
    (this multiple choice question has been scrambled)
  58. Place the following in order of lowest to highest boiling point. Propanoic acid, 2-butanone, diethyl ether, butanal, 1-butanal, pentane
    • BP (C) - Name
    • 34 - diethyl ether
    • 36 - pentane
    • 76 - butanal
    • 80 - 2-butanone
    • 117 - 1-butanol
    • 141 - propanoic acid

    All of the above compounds have comparable molecular weights... the key is in their polarity. The more polar, the stronger the hydrogen bonds, the higher the boiling points.
  59. Hemiacetal
    A molecule containing a carbon bonded to one -OH group and one -OR group; the product of adding one molecule of alcohol to the carbonyl group of an aldehyde or ketone.
  60. The product of adding one molecule of alcohol to the carbonyl group of an aldehyde or ketone.
    Hemiacetal
  61. Acetal
    A molecule containing two -OR groups bonded to the same carbon
  62. Unbranched carboxylic acids having between 12 and 20 carbon atoms are known as ______.
    Fatty acids
  63. Cyclic esters are called ____.
    Lactones
  64. Cyclic amides are called _____.
    lactams
  65. Step-growth polymers
    Step-growth polymers form from the reaction of molecules containing two functional groups, with each new bond being created in a separate step.
  66. How do we prepare esters?
    The most common laboratory method for the preparation of esters is Fischer esterification
  67. How do we prepare amides?
    Amides can be prepared by the reaction of an amine with a carboxylic anhydride.
  68. Hydrolysis
    Hydrolysis is a chemical process in which a bond is split and the elements of H2O are added.
  69. Anomers
    Monosaccharides that differ in configuration only at their anomeric carbons.
  70. Solid animal fats contain mainly ____ fatty acids, whereas vegetable oils contain high amounts of _____ fatty acids.
    Solid animal fats contain mainly saturated fatty acids, whereas vegetable oils contain high amounts of unsaturated fatty acids.
  71. Plants use the carbohydrate _____ for energy storage, and animals use the carbohydrate _____ for storing energy.
    Plants use the carbohydrate cellulose for energy storage, and animals use the carbohydrate glycogen for storing energy.
  72. What are the major roles of lipids?
    Storage: Energy stored in the form of fats.

    Membrane Components: The nonpolar portion of lipids provide the water-repellent, or hydrophobic property

    • Messengers: Chemical messagers
    • Primary messengers - deliver signals from one part of the body to another
    • Secondary messengers - Mediate the hormonal response
  73. Starch is composed of _____ and _____
    25% Amylose and 75% Amylopectin
  74. Amylose contains continuous ____ chains of D-Glucose.
    Amylopectin contains continuous _____ chanins of D-Glucose.
    • Amylose contains continuous unbranched chains of D-Glucose.
    • Amylopectin contains continuous branched chanins of D-Glucose.
  75. Sucrose is composed of _____ and _____
    Glucose and Fructose
  76. Maltose is composed of _____ and _____
    D-glucose and D-glucose
  77. Starch is hydrolyzed to _____
    Glucose
  78. Of the following compounds of similar molecular weight, which is the most soluble in water?

    A. butanoic acid
    B. 1-pentanol
    C. pentanal
    D. hexane
    A. butanoic acid
    (this multiple choice question has been scrambled)
  79. Which is the strongest organic acid of those with the pKa given below?

    A. 1.50
    B. 0.75
    C. 2.76
    D. 4.75
    B. 0.75
    (this multiple choice question has been scrambled)
  80. Which organic compound is the strongest acid of those given below?

    A. Acetic acid
    B. Chloroacetic acid
    C. Dichloroacetic acid
    D. Trichloroacetic acid
    D. Trichloroacetic acid
    (this multiple choice question has been scrambled)
  81. A compound containing two -OH groups is a _____.
    A compound with hydroxyl groups on adjacent carbons is a _____.
    • A compound containing two -OH groups is a diol
    • A compound with hydroxyl groups on adjacent carbons is a glycol
  82. Ethers react rapidly with which of the following?

    A. potassium dichromate
    B. almost nothing
    C. most acids
    D. H2
    B. almost nothing they make excellent solvents.
    (this multiple choice question has been scrambled)
  83. Thiols are most closely related to which of the following classes of compounds?

    A. carboxylic acids
    B. alcohols
    C. ketones
    D. aldehydes
    B. alcohols

    The functional group of a thiol is an -SH (sulfhydryl) group
    (this multiple choice question has been scrambled)
  84. Pencillin contains a cyclic amide; which of the following is the name for a cyclic amide?

    A. lactam
    B. anhydride
    C. thiol
    D. lactone
    A. lactam
    (this multiple choice question has been scrambled)
  85. What type of alcohol is formed by the hydration of 1-butene?

    A. secondary
    B. tertiary
    C. primary
    D. diol
    A. secondary

    Remember, "The rich get richer" one -H goes to the carbon with two Hs and the -OH goes to the carbon with only one H currently.
    (this multiple choice question has been scrambled)
  86. In organic compounds, which of the following elements normally forms two covalent bonds?

    A. nitrogen
    B. hydrogen
    C. carbon
    D. oxygen
    D. oxygen

    Carbon forms four, hydrogen one, and nitrogen three.
    (this multiple choice question has been scrambled)
  87. Which of the following functional groups does not contain a carbonyl group?

    A. ester
    B. ketone
    C. aldehyde
    D. alcohol
    D. alcohol

    Carbonyl group is a C double bonded to an O (C=O)
    (this multiple choice question has been scrambled)
  88. Dodecane is a 12-carbon alkane. How many hydrogen atoms are there in dodecane?

    A. 26
    B. 24
    C. 28
    D. 12
    A. 26
    (this multiple choice question has been scrambled)
  89. How many moles of molecular oxygen are consumed by the complete combustion of one mole of propane?

    A. 7
    B. 3
    C. 1
    D. 5
    D. 5

    Combustion equation

    C3H8 + 5 O2 --yields--> 3 CO2 + 4 H2O + heat
    (this multiple choice question has been scrambled)
  90. In a phenol, which group is the substituent on the benzene ring?

    A. amino
    B. carboxyl
    C. carbonyl
    D. hydroxyl
    D. hydroxyl
    (this multiple choice question has been scrambled)
  91. Generally, alkanes are _____ dense and _____ in water.

    A. more, soluble
    B. more, insoluble
    C. less soluble
    D. less, insoluble
    D. less, insoluble
    (this multiple choice question has been scrambled)

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