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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
enantiomer
ketone
ozonolysis
electrophilic addition of X2
2. If a compound is able to rotate plane polarized light.
optical activity
configuration
oxidizing
racemic mixture
3. Cleaves double bond in half - it only oxidizes the carbon to an aldehyde under reducing conditions. if ozidizing make same product as KMNO4
enantiomer
halogen
ozonolysis
disproportionation
4. Lowest priority group projects into the page
torsional strain
fischer projection
Haloalkane
chiral center
5. M - chloroperoxybenzoic acid
markovnikov's rule
anti conformation
electrophilic addition
mcpba
6. A = observed rotation / concentration * length
C3H8 + 5O2 = 3CO2 + 4H2O + heat
polymerization
specific rotation
pyrolysis
7. Sharing of electron between atoms
electrophilic addition of X2
cold potassium permanganate
covalent bond
Acetylene
8. Object that is not superimposable upon mirror image
chiral
electrophilic addition of X2
alkyne
catalytic hydrogenation
9. Carbon double bonded to an oxygen
quantum numbers
carbonyl
amines
carboxylic acid
10. Arise from angle strain - torsional strian and nonbonded strain
electrophilic addition of X2
meso compound
allyl
ring strain
11. Two p orbital form pi and third p orbital combine with s to make two sp hybrid. 180 degree apart
sp
electrophilic addition of X2
angle strain
triple bond
12. Carbon carbon triple bonds. Suffix-yne.
sp2
electrophile
Alkyne
sigma bond
13. More likely it is to attract positively charged proton. nucleophilic strength decreses: RO->HO>RCO2>ROH>H2O
initiation propagation termination
Ignored
basicity
configuration
14. Non mirror image of configurational isomers. cis and trans alkenes are them. possible when a molecule has two or more stereogenic centers that differ at some but not alll of the centers. they require multiple chiral centers.
torsional strain
diastereomers
Acetylene
pi bond
15. Same molecular formula but different structure
pyrolysis
peroxycarboxylic acid
isomer
carbonyl
16. Diol with hydroxyl group on same carbon
relative configuration
mcpba
geminal
lindlar's catalyst
17. Diols with hydroxyl group on adjacent carbon
racemic mixture
vicinal
pi bond
C3H8 + 5O2 = 3CO2 + 4H2O + heat
18. When boat flips
methylene
ring flip
combustion - disproportionation - free - radical substitution - pyrolysis
sp3
19. No double bonds. it has the maximum number of hydrogens.
hot - acidic potassium permanganate
saturated hydrocarbon
geometric isomers
ozonolysis
20. Most favorable of staggared conformations
anti conformation
Alkene
stereoisomers
basicity
21. In presence of peroxide - oxygen or ultraviolet light. antimarkonikov because they want a stable free radical. therefore X ends up on least subsituted carbon
electrophilic addition of free radicals
oxidation
geometric isomers
saturated hydrocarbon
22. 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-
eclipsed conformation
aldehyde
amines
pi bond
23. Propylenes attached to a backbone at the C-3 position. Meaning the double bond at end of the chain and single bonded carbon at rest
allyl
combustion - disproportionation - free - radical substitution - pyrolysis
ring strain
pi bond
24. Alkene oxidized with this - strong oxidizing agent. CH3CO3H or mcpba and it makes epoxide or oxirane
peroxycarboxylic acid
markovnikov's rule
ozonolysis
carbonyl
25. When a molecular orbital is formed head to head or tail to tail. all single bonds are tehese.
reducing
Ignored
sigma bond
covalent bond
26. Rotations cancel each other out therefore no optical activity
racemic mixture
sp3
disproportionation
halogen
27. Steps of free radical substitution
cold potassium permanganate
acetaldehyde
initiation propagation termination
aldehyde
28. Combustion reaction occurs through a radical process
relative configuration
acetaldehyde
C3H8 + 5O2 = 3CO2 + 4H2O + heat
aldehyde
29. Three different substitutents often have plane of symmetry. and rotation of 180 will allow molecule to be superimposed on mirror image
electrophilic addition of X2
achiral
electrophile
protic solvent
30. One s and three p orbitals
sp
disproportionation
quantum numbers
sp3
31. Fast process. double bond is nucleophile and attack x2. make cyclic halonium ion with either br or cl. and make dihalo trans
primary carbon
electrophilic addition of X2
covalent bond
hot - acidic potassium permanganate
32. Y = position of double bond - x is position of triple bond - root is the prefix representing the length of the principal carbon chain
relative configuration
quantum numbers
y- root - en -x-yne
sp3
33. Functionality is specified by alkoxy- prefix. ROR
achiral
ethers
oxidizing
electrophilic addition of HX
34. Nonterminal alkenes are cleaved to form two molar equivalent of carvoxylic acid ..make keton
hot - acidic potassium permanganate
vicinal
amines
electrophile
35. A molecule with an internal plane of symmetry
absolute configuration
aldehyde
meso compound
oxidizing
36. N - l - ml - ms
Vinyl
hot - acidic potassium permanganate
quantum numbers
chiral center
37. Use the Greek root for the number of carbons followed by the ending - - ane
Alkane nomenclature
acetaldehyde
potassium permanganate
sp3
38. Charged - need electrons
electrophile
halogenation
absolute configuration
gauche conformation
39. Chain of carbons connected by single bonds with hydrogen atoms attached.
diol
halogenation
enantiomer
Alkane
40. Refers to the =CH2 group
carboxylic acid
methylene
meso compound
allyl
41. Name for propanal
propionaldehyde
anti conformation
Haloalkane
pyrolysis
42. Goal is to produce most stable carbocation
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43. Palladium or barium sulfate (BaSO4) with quinoline. occur on metal surface - make cis.
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44. Name for ethanal
acetaldehyde
initiation propagation termination
C3H8 + 5O2 = 3CO2 + 4H2O + heat
nonbonded strain
45. Highest energy no separation. or 120 separation.
eclipsed conformation
Haloalkane
enantiomer
ionic bond
46. Iso - neo - cyclo
electrophile
pi bond
isomer
not ignored
47. Results when nonadjacent atoms or groups compete for space. dominant source of energy in flagpole interactions of the boat conformation. thus it goes in various conformations like chair boat and twist.
nonbonded strain
triple bond
enantiomer
Alkane nomenclature
48. Water can be added to alkenes under acidic conditions. make carbocation. ends with alcohol
racemic mixture
carboxylic acid
polymerization
electrophilic addition of H2O
49. Not solvated
relative configuration
aprotic solvent
specific rotation
chiral
50. 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
allyl
catalytic hydrogenation
C3H8 + 5O2 = 3CO2 + 4H2O + heat
pi bond
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