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Chp 6,7
Review
36
Chemistry
Undergraduate 2
11/04/2014

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Term
Chirality
Definition
Two mirror images of a chiral molecule are called enantiomers or optical isomers. Pairs of enantiomers are often designated as "right-" and "left-handed"
Term
Isomers
Definition
molecules with the same molecular formula but different chemical structures.
Term
Chiral objects
Definition
two mirror image
forms are not superposable upon one another.
Term
Achiral objects
Definition
two mirror image
forms are superposable.
Term
two different kinds of isomers
Definition
Constitutional isomers, and stereoisomers
Term
two different kinds of stereoisomers
Definition
Enantiomers and Diastereoisomers
Term
enantiomer
Definition
chiral molecules that are mirror images of one another. Furthermore, the molecules are non-superimposable on one another. This means that the molecules cannot be placed on top of one another and give the same molecule. Chiral molecules with one or more stereocenters can be enantiomers
Term
A stereogenic center
Definition
a carbon atom with four different groups attached to it. Can also be called: Chiral center, asymmetric center or a stereocenter
Term
A racemate or a racemic mixture
Definition
A mixture that contains equal quantities of enantiomers
Term
Properties of enantiomers
Definition
Same physical properties except that they rotate plane polarised light in opposite directions. Same chemical properties except when another chiral molecule is involved
Term
what is a meso achiral molecule?
Definition
A molecule that is split on its axis of symmetry and is superimposable when split
Term
Property of a small molecular weight organohalogen compound
Definition
This is a physical property that is volatile and have low boiling points
Term
organohalogen compounds
Definition
Most ___ ___ have higher densities than H2O and are insoluble in H2O
Term
resist.... They are useful for flame retardants, nonflammable solvents,fire suppressant chemicals, etc
Definition
In the chemical properties of organohalogens, many of them ___ combustion, with this information, what are they useful for?
Term
toxic , carcinogenic, harmful
Definition
When it comes to the biological activities of organohalogen compounds, many are ___ & ___, &/or ___ to the environment. (usually regulated)
Term
therapeutic, food additives , an example would be Splenda
Definition
When it comes to the biological activities of organohalogen compounds, some are used as ___ agents, or ___ ___. Name an example of this.
Term
Sn1
Definition
When chiral compounds undergo ___ reaction, they form a racemic mixture of enantiomers
Term
stable, resonance structure increase stability
Definition
This is a factor that affects the rate of Sn1, the more ___ the carbocation, the faster it can form, has a lower activation barrier. What is another thing that makes carbocations more stable?
Term
nucleophilic substitutions
Definition
Unlike aliphatic halides, aromatic halides do not readily under ___ ___ and other chemical reactions which lead to degradation of the structure - - this increases their persistence in plants and animals and in the environment in general.
Term
alkyl halides, , CFC's (chlorofluorocarbons), etc.
Definition
What are some examples of aliphatic halides?
Term
Aliphatic halides & Aromatic halides
Definition
What are the 2 chemical classifications of organohalogen compounds?
Term
DDT, PCB's, dioxin aka TCDD, etc.
Definition
What are some examples of aromatic halides?
Term
DDT
Definition
___ is a colorless, crystalline, tasteless and almost odorless organochloride known for its insecticidal properties. Banned in the 1970's. Not extensively degraded
Term
TCDD aka dioxin
Definition
Very unusual range of toxicities ranging from hepatotoxicity and carcinogenicity to immune suppression and “chloracne”
Once described as “the most toxic synthetic organic compound known to man”, but its toxicity is very species dependent.
Current sources include incinerated medical wastes containing chlorinated plastics.
Extremely persistent (half-life ~ 6 yrs) to limited chemical reactivity, resistance to metabolism and lipophilic physical properties.
Term
PCB's aka Polychlorinated biphenyls
Definition
Widely used as insulating materials and for other uses based on resistance to combustion.
Many undesirable effects including carcinogenicity, reproductive and estrogenic effects.
Replaced by polybrominated diphenyl ethers (PBDPE’s), which unfortunately have similar effects.
Term
Aldrin, 2,4-D, 2,4,5-T
Definition
What are three examples of chlorinated herbicides and insecticides
Term
Homochirality in nature
Definition
In nature, D-glucose is preferred, L-amino acids is preferred. What is this known as?
Term
The racemic switch
Definition
This term is used when there has been the development and use of a single enantiomer, to avoid possible side effects, or no activity with the other enantiomer in drug development.
Term
Racemic mixture
Definition
the 50/50 of two enantiomers
Term
meso stereomer
Definition
A stereoisomer with a plane of symmetry, also known as achiral
Term
chlorinated methanes
Definition
___ ___ are produced during municipal water treatment
Term
CFC's (chlorofluorocarbons)
Definition
These are ozone depleting chemicals
Term
Sucralose (Splenda), Zoloft (antidepressant), Chloroquine (treatment of arthritis, HIV/AIDS, malaria) and plavix, (blood thinner)
Definition
Chlorinated compounds which are approved for food and medicated use
Term
Chloroethane (ethyl chloride)
Definition
Chlorinate compound approved for medical use putting topically on skin as an anesthetic
Term
mechlorethamine, chlorambuci, cyclophosphamide
Definition
Cytotoxic “alkylating agents”: anticancer agents (also immunosuprresants and carcinogens)
Term
T3, & T4
Definition
The only organohalogen compounds biosynthesized by the human body: thyroid hormones
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