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ppt 4 Flashcards

1
Q

aryl group – symbolized by

A

Ar

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2
Q

used to describe fragrant substances

A

aromatic compounds/arenes

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3
Q

from coal distillate

A

benzene

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4
Q

from cherries, peaches, and almonds

A

benzaldehyde

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5
Q

from tolu balsam

A

toluene

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6
Q
  • now used to describe cyclic organic compounds with:
  • high degree of unsaturation
  • remarkably stable and unreactive compared to alkenes
A

aromatic compunds/arenes

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7
Q

incorrectly believed that the double bonds of benzene rapidly shift back and forth

A

kekule

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8
Q

HUCKEL’S CRITERIA FOR AROMATICITY

  • Have one _p orbital on each of its atoms.
  • Be ___ or nearly ___, so that there is continuous overlap or nearly continuous
    overlap of all 2p orbitals of the ring.
  • Have 2, 6, 10, 14, 18, or so forth pi electrons in the cyclic arrangement of 2 p
    orbitals (4n+2 rule)
A

2p

planar

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9
Q

has a hydroxyl (-OH) group bonded to an sp3 hybridized C in aliphatic group

A

alcohols

ROH

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10
Q

has a hydroxyl (-OH) group bonded to an sp2 hybridized C in aromatic group

A

phenols

ArOH

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11
Q

a fuel additive, an industrial solvent, and a beverage

A

ethanol

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12
Q

a general disinfectant, commonly called carbolic acid

A

phenol

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13
Q
  • can be thought of as organic derivatives of water in which one hydrogen is replaced by organic components
  • have nearly the same geometry as water(approximately tetrahedral)
  • have higher boiling points than alkanes (form H-bonds)
  • both weakly basic and weakly acidic
A

alcohols and phenols

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14
Q

reversibly protonated by strong acids to yield oxonium ions, ROH2+

A

as weak lewis bases

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15
Q

protonate water in dilute aqueous solutions to yield H3O+ and alkoxide ion (RO-) or a phenoxide ion (ArO-)

A

as weak acids

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16
Q

compounds containing an oxygen atom bonded to two carbon atoms

  • can be thought of as organic derivatives of water in which both hydrogens are
    replaced by organic components
  • have nearly the same geometry as water(approximately tetrahedral)
  • have lower boiling points than alcohols and phenols (no H bonds)
A

ether

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17
Q

the familiar “ether” of medical use; frequently used as a reaction solvent; was once popular as an inhaled anesthetic

A

diethyl ether

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18
Q

cyclic ethers with a 3-membered ring

A

epoxides

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19
Q
  • behave differently from open-chain ethers or other cyclic ethers
  • more reactive than other ethers because of ring strain
  • used in making “epoxy” adhesives, resins, and coatings
A

epoxide

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20
Q
  • sulfur analog of alcohols
  • has a sulfhydryl/mercapto/thiol (-SH) group bonded to a hydrocarbon chain
  • characteristic stench
  • widespread in living organisms
A

thiols

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21
Q

due 3-methylbutane-1-thiol and but-2-ene-1-thiol

A

skunk scent

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22
Q
  • part of proteins and enzymes (e.g. cysteine residues)

UNDERGOES REDOX REACTION
* can be oxidized by mild reagents (e.g. bromine or iodine) to yield disulfides, R-S-S-R
* disulfides can be reduced back to thiols by treatment with Zn and acetic acid
* thiol–disulfide interconversion is a key part of numerous biological processes (cross
linking of peptide chains)

A

thiols

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23
Q
  • sulfur analog of ethers
  • widespread in living organisms
A

thioethers/sulfides

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24
Q
  • derivatives of ammonia (NH3) in which one or more hydrogens are replaced by alkyl or aryl groups
  • tetrahedral geometry
  • have various applications in the chemical industry as starting materials for preparation
    of insecticides and pharmaceuticals
  • majority of pharmaceutical agents contain
  • many of the common coenzymes necessary for biological catalysis

CHARACTERISTIC ODOR
* _______ – fish-like aroma
* _______ – putrid

A

amines

trimethylamine
diamine (putrescine)

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25
contribute to the flavors and aromas of many foods and assisting in the biological functions of many enzymes produced in large amounts for use as solvents and as starting materials to prepare a host of other compounds
aldehydes and ketones
26
a carbonyl group(C=O) bonded to a H atom(terminal carbonyl group)
aldehydes
27
a carbonyl group (C=O) bonded to 2 C atoms (nonterminal carbonyl group)
ketones
28
an aldehyde; is a coenzyme involved in a large number of metabolic reactions (e.g., transamination)
Pyridoxal Phosphate (PLP)
29
a steroid hormone w/ ketone group; secreted by the adrenal glands to regulate fat, protein, and carbohydrate metabolism
Cortisol (Hydrocortisone)
30
produced for use in building insulation materials and in the adhesive resins that bind particle board and plywood
Formaldehyde (H2C=O)
31
widely used as an industrial solvent
Acetone [(CH3)2C=O]
32
not electronegative enough to stabilize a negative charge (unlike carboxylic acids and derivatives) can’t act as leaving groups in nucleophilic substitution reactions polarized because of because of high electronegativity of oxygen relative to carbon * C – ____ polarized and electrophilic (Lewis acidic) * O – ____ polarized and nucleophilic (Lewis basic)
C=O group in aldehyde
33
- contain an acyl group (RCO-) bonded to an electronegative atom/substituent that can act as a leaving group in substitution reactions - contains a carboxyl group (carbonyl group anda hydroxyl group) - major products of biochemistry occurring under oxidizing conditions
carboxylic acid
34
* can stabilize a negative charge and therefore can act as leaving groups in substitution reactions (unlike aldehydes and ketones)
C=O group in carboxylic acid
35
the principal organic component of vinegar
acetic acid (CH3CO2H)
36
responsible for the rancid odor of sour butter
Butanoic Acid (CH3CH2CH2CO2H)
37
responsible for the aroma of goats (Latin caper, meaning “goat”) and dirty socks
Hexanoic Acid/Caproic Acid (CH3(CH2)4CO2H)
38
destructive distillation of ants
formic acid formica
39
vinegar
acetic acid acetum
40
dairy products
propionic acid pion, fat
41
butter (particularly if rancid)
butyric acid butyrum
42
valerian root
valeric acid
43
odor of goats
caproic acid caper
44
* has acyl group bonded to OR orOAr * formed from a carboxylic acid and an alcohol * pleasant-smelling liquids that are responsible for the fragrant odors of fruits and flowers
esters
45
- found in pineapple oil
methyl butanoate
46
- found in banana oil
isopentyl acetate
47
a commonly used solvent; plastic balloon odor
ethyl acetate
48
used as plasticizers to keep polymers from becoming brittle
dialkyl phthalates
49
* cyclic esters * common names based on number of members in the ring designated by Greek letters
lactone
50
* has an acyl group bonded to a trivalent nitrogen atom * formed from a carboxylic acid and ammonia/amines
amides
51
* abundant in living organisms—proteins, nucleic acids, and many pharmaceuticals have amidefunctional groups * the least reactive of the common acid derivatives * stable to the temperatures andaqueousconditions foundin living organisms
amide
52
2nd degree amide
lactam
53
* has an acyl group (RCO-) bonded to a halogen atom * formed from a carboxylic acid and a hydrogen halide * only found in laboratories but not in nature because of high reactivity
ACID/ACYL HALIDES
54
* has two acyl groups bonded to an oxygen atom * formed from 2 carboxylic acids with loss of water
ACID/ACYL HALIDES
55
* no carbonyl group but treated as carboxylic acid derivatives * analogous to carboxylic acids * have a carbon atom with three bonds to electronegative atoms * contain a multiple bond
nitrile
56
different connectivities of atoms
constitutional isomer
57
same connectivities of atoms
stereoisomers
58
due to rotation about single bonds
conformational isomers
59
due to restricted rotation
geometric isomers
60
two types of isomers
geometric and conformational isomers
61

CCP 3 (8 decks)

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