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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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This is a study tool. The 3 wrong answers for each question are randomly chosen from answers to other questions. So, you might find at times the answers obvious, but you will see it re-enforces your understanding as you take the test each time.
1. Carbon double bonded to an oxygen
isomer
chiral center
carbonyl
sp3
2. If a compound is able to rotate plane polarized light.
optical activity
enantiomer
triple bond
combustion - disproportionation - free - radical substitution - pyrolysis
3. Rotations cancel each other out therefore no optical activity
Alkane
racemic mixture
mcpba
potassium permanganate
4. Alkene oxidized with this - strong oxidizing agent. CH3CO3H or mcpba and it makes epoxide or oxirane
relative configuration
methylene
peroxycarboxylic acid
alkyne
5. 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
absolute configuration
acetaldehyde
quantum numbers
pyrolysis
6. 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
oxidizing
protic solvent
ozonolysis
mcpba
7. Functionality is specified by alkoxy- prefix. ROR
ethers
stereoisomers
hybridization
Alkane
8. Name for ethanal
acetaldehyde
Ignored
torsional strain
ring strain
9. Alphabetical order of alkane rxn
aldehyde
combustion - disproportionation - free - radical substitution - pyrolysis
angle strain
reducing
10. Carbon with four different substituents and lack a plane of symmetry
aldehyde
pyrolysis
chiral center
optical activity
11. Hydrocarbon with one or more carbon carbon triple bond
alkyne
racemic mixture
pyrolysis
primary carbon
12. When bond angles deviate from ideal values
weak bases
angle strain
electrophilic addition of H2O
hybridization
13. Nonterminal alkenes are cleaved to form two molar equivalent of carvoxylic acid ..make keton
electrophilic addition of H2O
hot - acidic potassium permanganate
molecular orbital
oxidation
14. How many stereoisomers can a molecule have with n chiral centers
chiral center
2^n
electrophile
C3H8 + 5O2 = 3CO2 + 4H2O + heat
15. Zn/h or CH3/s with ozonolysis
ionic bond
optical activity
markovnikov's rule
reducing
16. Lowest priority group projects into the page
geminal
fischer projection
sigma bond
2^n
17. Di - tri - t - sec - n -
Ignored
sigma bond
basicity
primary carbon
18. Carbon carbon triple bonds. Suffix-yne.
mcpba
saturated hydrocarbon
Alkyne
electrophile
19. Monosubstituted ethylene
electrophilic addition of free radicals
Vinyl
alkyne
ionic bond
20. When two p orbitals line up in parallel and electron clouds overlap. it exsits over a single bond.
cold potassium permanganate
combustion - disproportionation - free - radical substitution - pyrolysis
Vinyl
pi bond
21. Diols with hydroxyl group on adjacent carbon
oxidation
Alkane
catalytic hydrogenation
vicinal
22. Creation of long - high molecular weight polymer composed of repeating subunit called monomers. occur through a radical mechanism.
halogen
polymerization
allyl
primary carbon
23. Is bonded to only one other carbon atom
covalent bond
ozonolysis
eclipsed conformation
primary carbon
24. Object that is not superimposable upon mirror image
combustion - disproportionation - free - radical substitution - pyrolysis
chiral
anti conformation
isomer
25. Same chemical formula. same atomic connectivity . different in how atoms are arranged in space
weak bases
Ignored
stereoisomers
optical activity
26. Arise from angle strain - torsional strian and nonbonded strain
ring strain
peroxycarboxylic acid
hybridization
specific rotation
27. A = observed rotation / concentration * length
protic solvent
potassium permanganate
specific rotation
oxidation
28. E of double bond act as lewis base and react with hydrogen of hx. make carbocation intermediate. use markonikovs rule
isomer
ozonolysis
achiral
electrophilic addition of HX
29. Diborane add to double bond. boron acts as lewis acid and attaches to less hindered carbon. hydride transferred to adjacent carbon. antimarkonikov - alcohol produced
oxidizing
hydroboration
conformational isomer
stereoisomers
30. M - chloroperoxybenzoic acid
mcpba
enantiomer
pi bond
oxidizing
31. A molecule with an internal plane of symmetry
ring strain
quantum numbers
combustion - disproportionation - free - radical substitution - pyrolysis
meso compound
32. A sigma bond and two pi bonds
covalent bond
oxidation
triple bond
ozonolysis
33. What is produced when o3 with lialh4 or nabh4
diastereomers
chiral center
alcohol
halogenation
34. Always receive number one. contain carbonyl and OH group - very oxidized. highest priority functional group.
carbonyl
racemic mixture
saturated hydrocarbon
carboxylic acid
35. 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
halogen
enantiomer
Alkane
electrophilic addition of H2O
36. N - l - ml - ms
achiral
absolute configuration
weak bases
quantum numbers
37. When boat flips
primary carbon
cold potassium permanganate
alkyne
ring flip
38. 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.
achiral
methylene
Combustion
molecular orbital
39. No double bonds. it has the maximum number of hydrogens.
relative configuration
polymerization
alcohol
saturated hydrocarbon
40. Compounds with halogen
Haloalkane
covalent bond
quantum numbers
C3H8 + 5O2 = 3CO2 + 4H2O + heat
41. In which one or morehydrogen atoms are replaced with a halogen atom. via free radical substitution
Alkane nomenclature
electrophilic addition of free radicals
amines
halogenation
42. Two hydroxyl groups
diol
saturated hydrocarbon
allyl
initiation propagation termination
43. Use the Greek root for the number of carbons followed by the ending - - ane
methylene
cold potassium permanganate
Alkane nomenclature
diastereomers
44. 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
catalytic hydrogenation
peroxycarboxylic acid
not ignored
geometric isomers
45. Refers to the =CH2 group
methylene
optical activity
eclipsed conformation
not ignored
46. Steps of free radical substitution
aprotic solvent
initiation propagation termination
quantum numbers
anti conformation
47. 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.
halogenation
diastereomers
racemic mixture
Vinyl
48. One s and three p orbitals
structural isomers
acetaldehyde
sp3
aprotic solvent
49. 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
aprotic solvent
weak bases
ozonolysis
50. Ozonolysis under hot acidic kmO4 - e.g. H2O2 condition
formaldehyde
oxidizing
configuration
enantiomer
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