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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. Water can be added to alkenes under acidic conditions. make carbocation. ends with alcohol
enantiomer
electrophilic addition of H2O
sp
conformational isomer
2. Alphabetical order of alkane rxn
weak bases
sigma bond
combustion - disproportionation - free - radical substitution - pyrolysis
Alkane nomenclature
3. Common name for ethyne
enantiomer
electrophilic addition of HX
Acetylene
diastereomers
4. 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
polymerization
sp3
Acetylene
5. Ozonolysis under hot acidic kmO4 - e.g. H2O2 condition
ozonolysis
saturated hydrocarbon
combustion - disproportionation - free - radical substitution - pyrolysis
oxidizing
6. Not solvated
Haloalkane
hot - acidic potassium permanganate
aprotic solvent
weak bases
7. Carbon carbon triple bonds. Suffix-yne.
disproportionation
halogen
electrophilic addition of HX
Alkyne
8. Creation of long - high molecular weight polymer composed of repeating subunit called monomers. occur through a radical mechanism.
electrophilic addition of free radicals
polymerization
Vinyl
isomer
9. When two p orbitals line up in parallel and electron clouds overlap. it exsits over a single bond.
allyl
anti conformation
pi bond
ozonolysis
10. Carbon with four different substituents and lack a plane of symmetry
oxidizing
vicinal
nonbonded strain
chiral center
11. Same molecular formula but different structure
gauche conformation
hot - acidic potassium permanganate
potassium permanganate
isomer
12. Configuration in relation to another chiral molecule. use it to determine if a molecule is an enantiomer - diastereomer - etc
markovnikov's rule
relative configuration
racemic mixture
potassium permanganate
13. F - CL - Br - I
halogen
stereoisomers
torsional strain
oxidation
14. When boat flips
ring flip
triple bond
fischer projection
y- root - en -x-yne
15. Cleaves double bond in half - it only oxidizes the carbon to an aldehyde under reducing conditions. if ozidizing make same product as KMNO4
ozonolysis
electrophile
Vinyl
2^n
16. 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-
carbonyl
amines
aprotic solvent
potassium permanganate
17. A molecule with an internal plane of symmetry
electrophilic addition of free radicals
meso compound
Alkene
peroxycarboxylic acid
18. Most favorable of staggared conformations
ethers
optical activity
anti conformation
Alkane nomenclature
19. Object that is not superimposable upon mirror image
electrophilic addition
chiral
aprotic solvent
allyl
20. Fast process. double bond is nucleophile and attack x2. make cyclic halonium ion with either br or cl. and make dihalo trans
relative configuration
protic solvent
electrophilic addition of X2
Vinyl
21. Iso - neo - cyclo
potassium permanganate
formaldehyde
not ignored
quantum numbers
22. What is produced when o3 with lialh4 or nabh4
Alkyne
chiral center
alcohol
protic solvent
23. 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
combustion - disproportionation - free - radical substitution - pyrolysis
sp
catalytic hydrogenation
Vinyl
24. Kmno4
hydroboration
potassium permanganate
polymerization
sp2
25. Diols with hydroxyl group on adjacent carbon
vicinal
Acetylene
halogen
potassium permanganate
26. 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.
methylene
ethers
diastereomers
markovnikov's rule
27. Steps of free radical substitution
vicinal
enantiomer
ionic bond
initiation propagation termination
28. Two p orbital form pi and third p orbital combine with s to make two sp hybrid. 180 degree apart
diastereomers
sp
Acetylene
fischer projection
29. What are the best leaving groups?
sp
hydroboration
weak bases
saturated hydrocarbon
30. Carbon double bonded to an oxygen
ozonolysis
conformational isomer
structural isomers
carbonyl
31. Electrons of pi bond are reactive and easily attacked by molecules that want e pair e.g. electrophiles.
electrophilic addition
halogen
pi bond
Alkyne
32. When bond angles deviate from ideal values
pyrolysis
angle strain
ring flip
torsional strain
33. Always receive number one. contain carbonyl and OH group - very oxidized. highest priority functional group.
carboxylic acid
propionaldehyde
pyrolysis
absolute configuration
34. One s and two p 120 degree apart
methylene
basicity
oxidation
sp2
35. Goal is to produce most stable carbocation
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36. In presence of peroxide - oxygen or ultraviolet light. antimarkonikov because they want a stable free radical. therefore X ends up on least subsituted carbon
Alkane
electrophilic addition of free radicals
carbonyl
ring strain
37. 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
propionaldehyde
sp3
ozonolysis
38. Use the Greek root for the number of carbons followed by the ending - - ane
sp2
Alkane nomenclature
diastereomers
pyrolysis
39. How many stereoisomers can a molecule have with n chiral centers
meso compound
ring strain
2^n
acetaldehyde
40. Arise from angle strain - torsional strian and nonbonded strain
eclipsed conformation
ring strain
amines
electrophile
41. Results when cyclic molecules must assume conformations that have eclipsed interactions
formaldehyde
specific rotation
not ignored
torsional strain
42. Hydrocarbon with one or more carbon carbon triple bond
basicity
aprotic solvent
electrophilic addition of free radicals
alkyne
43. Is bonded to only one other carbon atom
primary carbon
alcohol
protic solvent
electrophilic addition of HX
44. No double bonds. it has the maximum number of hydrogens.
diol
saturated hydrocarbon
isomer
disproportionation
45. Diol with hydroxyl group on same carbon
geminal
2^n
racemic mixture
oxidation
46. Lowest priority group projects into the page
fischer projection
electrophilic addition of H2O
sp3
electrophilic addition
47. Alkenes oxidzed with kmno4 - if made with cold - dilue - make OH on each side of double bond - diols or glycol in syn orientation
geometric isomers
cold potassium permanganate
relative configuration
ozonolysis
48. Carbonyl located in middle or somewhere in chane. Named with One
geometric isomers
relative configuration
alkyne
ketone
49. Alkene oxidized with this - strong oxidizing agent. CH3CO3H or mcpba and it makes epoxide or oxirane
peroxycarboxylic acid
methylene
specific rotation
vicinal
50. Sharing of electron between atoms
covalent bond
oxidation
y- root - en -x-yne
Combustion
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