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24 Cards in this Set

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(T/F) Achiral molecules have an internal plane of symmetry.
True.
(T/F) Diastereomers may have different melting points.
True.
(T/F) Diastereomers may have different retention times on a gas chromatogram.
True.
(T/F) Diastereomers may have different optical rotations.
True
When looking for diastereomers, what should you do?
Find the configuration and look for the opposite; ie. if you have (R,R,S), then look for (S,S,R).
(T/F) In order to be a meso compound, there must contain stereocenters.
TRUE; carbon must be bonded to four unique substituents.
The tosylate group is a better leaving group than the hydroxyl group due to...
After acting as a leaving group, the tosylate or hydroxyl group will be negatively charged. The tosylate is able to stabilize this charge by distributing it by resonance.
What is the thio functional group?
-SH
What is the acetylene group?
C triple bonded to C
What is the process of separating two enantiomers from each other?
resolution
Why is CH3CH2)3CBr a better leaving group than(CH3CH2)3CF?
Bromine is a better leavin ggroup than fluorine due to its larger size and is more likely to undergo an SN1 reaction.
Which one of the folloiwn gmolecules will most easily undergo an SN2 reaction? CH3I or CH3F.
CH3I since iodine is a better leaving group than fluorine due to its larger size.
(T/F) E1 reactions are characterized by a nucleophilic attack on a carbocation intermediate.
False;
- E1 reactiosn begin with breaking of a carbon-leaving group bond to form a carbocation intermediate. In a second step, deprotonation of an alpha-hydrogen by a base results in the formation of a pi bond.
- Nucleophilic attack on the carbocation is characteristic of SN1 reactions.
Alkane halogenation reactions proceed by which of the following mechanisms.
a. free radical halogenation.
b. sn1
c. sn2
d. E1
Since alkanes hav eno potential leaving group, they don't undergo SN1, SN2, or E1 reactions. Halogenation of alkanes is accomplished by free radical halogenation.
The use of light indicates what?
a radical reaction
What should you think of whenever you see something like KOC(CH3)3.
This is a bulky base so it should promote elimination reactions of molecules bearing leaving groups.
What does thionyl chloride do?
it converts alcohols into the corresponding alkyl chlorides.
(T/F) A Sn2 reaction that occurs when hydroxide ion is added to an alkyl halide is considerable slowed when the reaction mixture isplaced in a solvent possibly b/c the solvent solvates the hydroxide ion.
Solvation of the starting material, therby stabilizing it, increases the activation barrier and slows the reaction rate.
(T/F) Nucleophiles are "nucleus seeking" species that have either a full negative formal charge or a partial negative charge.
TRUE.
When ethanol is exposed to SOCl2, the compounds undergo?
- addition, elimination, and then substitution to form chloroethane.
- First an addition-elimination sequence occurs to the S=O double bond, then substitution by Cl- at C-1 of the alcohol gives the product (chloroethane).
A quaternary ammonium salt doesn't carry out substitution reactions with alkyl halides b/c the nitrogen atom is is electrophilic.
TRUE;
electrophiles are species that usually have either a full formally positive charge or a partial positive charge.
Is cyclodecane planar?
No, just like all other nonaromatic rings, its puckered and twisted to allow bond angles to be close to 109 degrees.
(T/F) When reacting with ALKENES, bromine radicals tend to add to the most substituted carbon of the double bond.
FALSE;
- Bromine radicals tend to add to the LEAST substituted carbon of the double bond which is the reverse of the case with alkanes.
(T/F) For alkanes, free radical bromination occurs at the most substituted position.
True. However for alkenes, its added to the least substittued carbon of the double bond.