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MCAT Organic Chemistry
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Subjects
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mcat
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science
Instructions:
Answer 50 questions in 15 minutes.
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Match each statement with the correct term.
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1. Moleculse that have the opposite configuration at their one chiral center. or if multiple chiral centers - must have the opposite configuration at every one of their chiral centers to be enantiomers. identical physical properties and much of the same
geometric isomers
acetaldehyde
oxidizing
enantiomer
2. Cleaves double bond in half - it only oxidizes the carbon to an aldehyde under reducing conditions. if ozidizing make same product as KMNO4
fischer projection
ozonolysis
electrophile
Combustion
3. Common name for ethyne
gauche conformation
Acetylene
configuration
absolute configuration
4. F - CL - Br - I
halogen
absolute configuration
meso compound
chiral
5. Diborane add to double bond. boron acts as lewis acid and attaches to less hindered carbon. hydride transferred to adjacent carbon. antimarkonikov - alcohol produced
ethers
electrophilic addition
ketone
hydroboration
6. Is bonded to only one other carbon atom
2^n
ring flip
primary carbon
Alkyne
7. Steps of free radical substitution
Combustion
halogenation
initiation propagation termination
aprotic solvent
8. No double bonds. it has the maximum number of hydrogens.
saturated hydrocarbon
disproportionation
eclipsed conformation
carbonyl
9. E of double bond act as lewis base and react with hydrogen of hx. make carbocation intermediate. use markonikovs rule
electrophilic addition of HX
ionic bond
not ignored
meso compound
10. Always receive number one. contain carbonyl and OH group - very oxidized. highest priority functional group.
methylene
carboxylic acid
eclipsed conformation
carbonyl
11. Reaction of alkane with oxygen to form carbon dioxide - water and heat.
halogenation
mcpba
sp2
Combustion
12. Most favorable of staggared conformations
structural isomers
anti conformation
diol
electrophile
13. Solvents with protons in solution - e.g. water or alcohol. large atoms tend to be better nucleophiles in here because they can shed the solvating protons around them and are more polarizable
protic solvent
covalent bond
Alkyne
sp
14. Nitrogen containing compound - longest chain attached to nitrogen used in backbone. use e and replace with AMINE. if more complex molecule present - use prefix amino. IF additional group added - use N-
amines
electrophilic addition
hydroboration
gauche conformation
15. Ozonolysis under hot acidic kmO4 - e.g. H2O2 condition
pi bond
peroxycarboxylic acid
oxidizing
diastereomers
16. What are the best leaving groups?
diastereomers
methylene
covalent bond
weak bases
17. N - l - ml - ms
relative configuration
quantum numbers
allyl
configuration
18. Reducing an alkene by adding molecular hydrogen to double bond with aid of metal catalyst. e.g. pt - pd - ni. takes place on surface of metal so it does syn addition
pi bond
Vinyl
acetaldehyde
catalytic hydrogenation
19. Water can be added to alkenes under acidic conditions. make carbocation. ends with alcohol
cold potassium permanganate
amines
electrophilic addition of H2O
meso compound
20. How many stereoisomers can a molecule have with n chiral centers
Acetylene
lindlar's catalyst
nonbonded strain
2^n
21. Highest energy no separation. or 120 separation.
2^n
hydroboration
mcpba
eclipsed conformation
22. A molecule with an internal plane of symmetry
not ignored
carboxylic acid
cold potassium permanganate
meso compound
23. Creation of long - high molecular weight polymer composed of repeating subunit called monomers. occur through a radical mechanism.
electrophilic addition of free radicals
polymerization
Alkane
lindlar's catalyst
24. Configuration in relation to another chiral molecule. use it to determine if a molecule is an enantiomer - diastereomer - etc
propionaldehyde
relative configuration
geometric isomers
ketone
25. More likely it is to attract positively charged proton. nucleophilic strength decreses: RO->HO>RCO2>ROH>H2O
configuration
basicity
fischer projection
gauche conformation
26. Use the Greek root for the number of carbons followed by the ending - - ane
protic solvent
Alkane nomenclature
allyl
polymerization
27. Object that is not superimposable upon mirror image
catalytic hydrogenation
ionic bond
amines
chiral
28. Di - tri - t - sec - n -
Ignored
Haloalkane
combustion - disproportionation - free - radical substitution - pyrolysis
sigma bond
29. When two atomic orbitals combine. obtained mathematically by adding or subtracting wave functions. if sings are the same - make bonding - if different - less stable antibonding.
enantiomer
sigma bond
anti conformation
molecular orbital
30. Hydrocarbon with one or more carbon carbon triple bond
primary carbon
alkyne
configuration
aldehyde
31. Describes the exact spatial arrangement of groups of atoms independent of other molecules.
carboxylic acid
angle strain
allyl
absolute configuration
32. Same molecular formula but different structure
electrophilic addition of H2O
ozonolysis
isomer
Alkane nomenclature
33. Spatial arrangement of the atoms or groups of a sterioisomer
Vinyl
saturated hydrocarbon
ring strain
configuration
34. Rotations cancel each other out therefore no optical activity
specific rotation
ring strain
basicity
racemic mixture
35. A radical transfers a hydrogen atom to another radical and makes an alkane and alkene
disproportionation
geminal
sp
protic solvent
36. Combustion reaction occurs through a radical process
C3H8 + 5O2 = 3CO2 + 4H2O + heat
lindlar's catalyst
hybridization
methylene
37. Charged - need electrons
torsional strain
isomer
electrophile
ring strain
38. Fast process. double bond is nucleophile and attack x2. make cyclic halonium ion with either br or cl. and make dihalo trans
propionaldehyde
electrophilic addition of X2
allyl
anti conformation
39. Kmno4
basicity
markovnikov's rule
disproportionation
potassium permanganate
40. Alphabetical order of alkane rxn
aprotic solvent
combustion - disproportionation - free - radical substitution - pyrolysis
triple bond
alkyne
41. One s and two p 120 degree apart
sp2
ozonolysis
relative configuration
triple bond
42. Carbon carbon triple bonds. Suffix-yne.
initiation propagation termination
Haloalkane
halogenation
Alkyne
43. Nonterminal alkenes are cleaved to form two molar equivalent of carvoxylic acid ..make keton
Ignored
hot - acidic potassium permanganate
acetaldehyde
electrophile
44. Two p orbital form pi and third p orbital combine with s to make two sp hybrid. 180 degree apart
diol
Combustion
sp
carbonyl
45. When two p orbitals line up in parallel and electron clouds overlap. it exsits over a single bond.
electrophilic addition of free radicals
pi bond
racemic mixture
achiral
46. Name for ethanal
acetaldehyde
not ignored
2^n
hybridization
47. Arise from angle strain - torsional strian and nonbonded strain
isomer
ozonolysis
ring strain
hot - acidic potassium permanganate
48. If reagent has a bunch of oxygen
ozonolysis
oxidation
aprotic solvent
quantum numbers
49. Carbonyl located at the end of the chain named by replacing al with e. e.g. butanal
molecular orbital
aldehyde
chiral
basicity
50. Occur when a molecule is broken down by heat. used to reduce the avverage molecular weight of heavy oils. c - c - bonds are cleave dand make small chain alkyl radicals that recombine to form different alkanes
pyrolysis
potassium permanganate
isomer
methylene
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