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Organic Chemistry Chap. 5 & 6 True and False
True and false pertaining to test 3
50
Organic Chemistry
Undergraduate 2
10/12/2011

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Term
A chiral object is superposable on its mirror image.
Definition
F
Term
Stereoisomers are one type of constitutional isomers.
Definition
F
Term
trans-1,2-dichloroethene has an enantiomeric relationship to the cis isomer.
Definition
F
Term
Disastereomers are stereoisomers which are not mirror images of each other.
Definition
T
Term
2-Chloroheptane is achiral while 4-chloroheptane is not.
Definition
F
Term
Chiral molecules usually have a plane of symmetry.
Definition
F
Term
The (R) enantiomer of chiral compound usually rotates the plane of polarized light to the left.
Definition
F
Term
The nickel catalyzed hydrogenation of butanone produces (S)-2-butanol.
Definition
F
Term
The meso form of a molecule can be either dextrorotatory of levorotatory.
Definition
F
Term
trans-1,4-dimethlycyclohexane is achiral while the cis-isomer is chiral.
Definition
T
Term
3-ethylcyclohexene is chiral.
Definition
T
Term
An equimolar mixture of enantiomers is called a racemic mixture.
Definition
T
Term
A plane of symmetry is defined as an imaginary plane that bisects a molecule in such a way that the two halves of the molecule are mirror images of each other.
Definition
T
Term
In the R,S system, a t-butyl substituent has a lower priority than an isobutyl substituent.
Definition
F
Term
In compounds whose stereoisomerism is due to chirality centers, the total number of stereoisomers will not exceed 2^n, where n is equal to the number of chirality centers.
Definition
T
Term
Diastereomers have different physical and chemical properties.
Definition
T
Term
Enantiomers can be easily separated by distillation or crystallization because their properties are different.
Definition
F
Term
1,3-dibromoallene is chiral.
Definition
T
Term
cos-1,3-dichlorocyclobutane is chiral.
Definition
F
Term
Increasing the concentration of the nucleophilic species in an Sn1 reaction increases the rate of reaction.
Definition
F
Term
Carbocations are nucleophilic Lewis bases.
Definition
F
Term
The Sn2 reaction occurs by a back-side attack of the nucleophile on the chiral carbon bearing the leaving group. The results in retention of configuration at a chiral center.
Definition
F
Term
The difference in free energy between the reactants and the products is defined as the free energy of activation.
Definition
F
Term
The smaller the free energy of activation the slower the reaction.
Definition
F
Term
The overall rate in a multi-step reaction is controlled primarily by the slowest step in the reaction sequence.
Definition
T
Term
The first step in the Sn1 reaction of tert-butyl chloride is the homolytic cleavage of the carbon-chlorine bond.
Definition
F
Term
Carbocations have a trigonal planar geometry at the carbon bearing the positive charge.
Definition
T
Term
Carbon-hydrogen and carbon-carbon bonds located beta to a carbocationic center stabilize the cationic species by hyperconjugative electron delocalization.
Definition
T
Term
The Hammond-Leffler postulate states that the structure of a transition state resembles the stable species that is nearest it in free energy.
Definition
T
Term
Nucleophilicities are related to rates of reaction while basicities are related to equilibria.
Definition
T
Term
Dimethylsulfoxide and N,N-dimethylformamide are dipolar protic solvents.
Definition
F
Term
The Sn2 reaction is an example of a one-steop non-concerted reaction.
Definition
F
Term
The tert-butyl cation is less stable than the isopropyl cation.
Definition
F
Term
The reaction of tert-butyl chloride with methanol is an example of a methanolysis reaction.
Definition
T
Term
Secondary alkyl halides undergo Sn2 reactions more readily than primary alkyl halides.
Definition
F
Term
Neopentyl halides even though they are primary halides, are very unreactive in an Sn2 nucleophilic displacement due to steric effects.
Definition
T
Term
In polar, aprotic solvents such as dimethylsulfoxide, fluoride is a poorer nucleophile than iodide.
Definition
F
Term
In substitution reactions triflate is a poorer leaving group than p-toluenesulfonate.
Definition
F
Term
Vinyl chloride is a molecule where the chloride is attached to an sp hybridized carbon.
Definition
F
Term
A secondary carbocation is more stable than a vinyl carbocation.
Definition
T
Term
In an Sn2 reaction bromide is a better leaving group compared to chloride.
Definition
T
Term
In an Sn2 reaction bromide is a better nucleophile compared to iodide.
Definition
T
Term
tert-Butyl chloride undergoes an Sn1 process at a faster rate than sec-butyl chloride.
Definition
T
Term
Nucleophiles are species with at least one unshared electron pair.
Definition
T
Term
Nucleophiles are Lewis acids.
Definition
F
Term
In general, Sn2 reactions are characterized by 2nd-order kinetics.
Definition
T
Term
A concerted reaction is one in which there is a single energy barrier between the reactants and products.
Definition
T
Term
Sn2 reactions at a chiral center always occurs with inversion of configuration.
Definition
T
Term
The reaction of tert-butyl chloride with sodium methoxide in methanol leads to the formation of tert-butyl methyl ether.
Definition
F
Term
1-Bromo[2.2.1]bicycloheptane, a tert halide, undergoes rapid ethanolysis.
Definition
F
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