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Study sets matching "ochem 3"

27 terms
OChem 3
Z
E
Primary Carbon
Secondary Carbon
An alkene with the higher substituent groups on the same side…
An alkene with the higher substituent groups on opposite side…
A carbon with 2 R group and 2 H
A carbon with 2 R groups and 1 H
Z
An alkene with the higher substituent groups on the same side…
E
An alkene with the higher substituent groups on opposite side…
141 terms
OCHEM 3
Hydrogenation
Reactions with water
Ester are one class of molecule that u…
Catalyst
Dehydration:... Remove water (OH+H),creates new bond... Hydrolysis…
When an Ester is treated with water in the presence of H+,a c…
A catalyst is a substance that speeds up a reaction without i…
Hydrogenation
Reactions with water
Dehydration:... Remove water (OH+H),creates new bond... Hydrolysis…
33 terms
OCHEM 3
Nucleophile
electrophile
strong nucleophiles
LDA
- Lewis Base... - electron pair donor... - negative charge, partial…
- Lewis Acid... - electron pair acceptor... - positive charge, part…
OH-... RO-... R2N-... R-NH2... CN-
strong base
Nucleophile
- Lewis Base... - electron pair donor... - negative charge, partial…
electrophile
- Lewis Acid... - electron pair acceptor... - positive charge, part…
20 terms
ochem 3
Ammonium Salts... (Functional Group Pictu…
Ammonium Salts ... (Non-covalent Interact…
Ammonium Salts... (Reason for Boiling Poi…
Ammonium Salts... (Reason for Water Solub…
As salts, they are held together by ionic bonds, which are fa…
Salts make Ionic bonds which being real bonds are much strong…
Salt is composed of a cation (ammonium ion) and an anion, and…
Ammonium Salts... (Functional Group Pictu…
Ammonium Salts ... (Non-covalent Interact…
As salts, they are held together by ionic bonds, which are fa…
40 terms
ochem 3
curved arrows
first step for drawing curved arrows
structures with both - and +
structures with only C-H... carbohydrates
go from electron rich (-) to electron poor (+)... move electron…
expand structure to show all H bonds... note how many bonds bein…
1. draw arrow from atom with - charge to bond nearest to atom…
1. draw arrow from double bond to bond connected to atom with…
curved arrows
go from electron rich (-) to electron poor (+)... move electron…
first step for drawing curved arrows
expand structure to show all H bonds... note how many bonds bein…
36 terms
OChem Exam 3
Cleave Alkene (Ozonolysis)
Primary Alcohol -> Aldehyde
Mild Permanganate Oxidation of Alkynes…
Cleave Alkyne
1. O3 ... 2. (CH3)2S
Swern Oxidation
KMnO4 H2O pH=7
1. KMnO4 KOH, heat ... 2. H3O+
Cleave Alkene (Ozonolysis)
1. O3 ... 2. (CH3)2S
Primary Alcohol -> Aldehyde
Swern Oxidation
27 terms
ochem3
H2SO4, H2O/HgSO4
9BBN/H2O2, NaOH
CO2 and acid
2 acids
ketone reagents
aldehyde reagents
terminal alkane treated with O3/H2O
internal alkane treated with O3/H2O
H2SO4, H2O/HgSO4
ketone reagents
9BBN/H2O2, NaOH
aldehyde reagents
10 terms
ochem 3
hydohalogenation
acid-catalyzed hydration
halogenation
halohydrin formation
syn and anti
syn and anti
anti
anti
hydohalogenation
syn and anti
acid-catalyzed hydration
syn and anti
8 terms
Ochem 3
Reacciones de éteres
Éteres con sustituyentesprimarios y se…
Éteres con sustituyentes terciarios
Éteres con exceso del ácido
Los éteres se protonan y son atacados por un nucleófilo
Reaccionan con HBr o HI y por SN2. El oxigeno se protona y el…
Se protona el oxígeno y se forma el carbocatión. El nucleófil…
Forman dos halo alcanos y agua
Reacciones de éteres
Los éteres se protonan y son atacados por un nucleófilo
Éteres con sustituyentesprimarios y se…
Reaccionan con HBr o HI y por SN2. El oxigeno se protona y el…
25 terms
ochem 3
hemi-acetal
NaBH4
lithium dialkylcuprate
Tollen's Reaction
geminal alkoxy-alcohol
demurcuration
forms ketone from acid halide
uses silver nitrate in aqueous ammonia
hemi-acetal
geminal alkoxy-alcohol
NaBH4
demurcuration
12 terms
OChem #3
NaOH
EtOH
CH3OH
NaCN
E2/SN2
E1/SN1
SN1/E1
SN2
NaOH
E2/SN2
EtOH
E1/SN1
64 terms
ochem 3
Absolute configuration
Achiral
Achirotopic
Anomers
A designation of the position or order of arrangement of the…
Not chiral. A necessary and sufficient criterion for achirali…
The opposite of chirotopic. See"chirotopic" below.
Diastereomers of glycosides or related cyclic forms of sugars…
Absolute configuration
A designation of the position or order of arrangement of the…
Achiral
Not chiral. A necessary and sufficient criterion for achirali…
21 terms
ochem 3
-NH2
-NHR
-NR2
-OR
sb/sn
sb/sn
sb/sn
sb/sn
-NH2
sb/sn
-NHR
sb/sn
OCHEM 3
Strong Activators
Moderate Activators
Weak Activators
Weak Deactivators
NH2... NHR... OH... OR
NH(C=O)R... O(C=O)R
R... Ar
F... Cl... Br... I
Strong Activators
NH2... NHR... OH... OR
Moderate Activators
NH(C=O)R... O(C=O)R
12 terms
OChem #3
Hydroboration-oxidation
X2 Addition to Alkene
Hydrogenation
Oxymercuration-Demercuration
syn
anti
syn
syn + anti
Hydroboration-oxidation
syn
X2 Addition to Alkene
anti
41 terms
Ochem 3
Heteroatoms
Functional Group
Hydrocarbons
Aliphatic Hydrocarbons
Atoms other than carbon or hydrogen
Structural features that determine a molecule's geometry, phy…
Compounds made up of only the elements carbon and hydrogen.
Alkanes, Alkenes, and Alkynes
Heteroatoms
Atoms other than carbon or hydrogen
Functional Group
Structural features that determine a molecule's geometry, phy…
118 terms
OChem 3
What is an amine?
How do amines usually participate in r…
Properties of amines
Which makes stronger hydrogen bonds: a…
any organic compound that contains a basic nitrogen atom
-amines can act as either bases or nucleophiles... -primary or s…
-melting point and boiling point increase with molecular weig…
Alcohols bc oxygen is more electronegative, and thus, it crea…
What is an amine?
any organic compound that contains a basic nitrogen atom
How do amines usually participate in r…
-amines can act as either bases or nucleophiles... -primary or s…
21 terms
Ochem 3
Alkene
Reactive bond of Alkene
Bulky bases give
Hoffman product
Double bonds
The 1pi bond
Hoffman product
Less substituted due to attack on less crowded H
Alkene
Double bonds
Reactive bond of Alkene
The 1pi bond
17 terms
ochem3
"non-bases"
Moderate bases
Strong Bases
SN1
H2O, ROH, RCO2H R2S, RSH, R3P, Cl, Br, I
NH3, RCO2-, -CN, RS- N3-
-OH, -OR, -C =-C-R
first 3 non bases
"non-bases"
H2O, ROH, RCO2H R2S, RSH, R3P, Cl, Br, I
Moderate bases
NH3, RCO2-, -CN, RS- N3-
20 terms
Ch. 3 ochem
constitutional isomers
primary carbon
secondary carbon
tertiary carbon
compounds that have the same molecular formula but the atoms…
carbon bonded to only one other carbon
carbon bonded to 2 other carbons
carbon bonded to 3 other carbons
constitutional isomers
compounds that have the same molecular formula but the atoms…
primary carbon
carbon bonded to only one other carbon
17 terms
Ochem Ch. 3
Brønsted-Lowry acid and bases
Brønsted-Lowry acid
Brønsted-Lowry base
Conjugate base
based on the transfers of a proton (H+)
proton donor
proton acceptor
negative charge
Brønsted-Lowry acid and bases
based on the transfers of a proton (H+)
Brønsted-Lowry acid
proton donor
33 terms
ochem3
ADME
Affinity
Analog
Combinatorial Synthesis
Absorbtion, Distribution, Metabolism, Excretion
Tendency of a molecule to associate with another
An analog is a drug whose structure is related to that of ano…
Synthesis starting with building blocks
ADME
Absorbtion, Distribution, Metabolism, Excretion
Affinity
Tendency of a molecule to associate with another
16 terms
Ochem Ch 3
alkane... R-H. R could be a methyl, ethyl…
alkene... functional group=double bond (C…
alkyne... functional group=triple bond (C…
aromatic ring... functional group=phenyl
What is this structure?
What is this structure?
What is this structure?
what is this structure?
alkane... R-H. R could be a methyl, ethyl…
What is this structure?
alkene... functional group=double bond (C…
What is this structure?
16 terms
OChem Quiz 3
1 C
2 C
3 C
4 C
meth
eth
pro
but
1 C
meth
2 C
eth
32 terms
Ochem3
True or False? A simple distillation,…
True or False? A simple distillation,…
True or False? A simple distillation,…
True or False? A simple distillation,…
False
True
False
False
True or False? A simple distillation,…
False
True or False? A simple distillation,…
True
27 terms
Ochem exam 3
nucleophile
electrophile
(Functional groups)
aldehyde
(- charge)... an electron rich species that donates an electron…
(+ charge)... an "electron lover" or substance that accepts an e…
...
(RCHO)
nucleophile
(- charge)... an electron rich species that donates an electron…
electrophile
(+ charge)... an "electron lover" or substance that accepts an e…
55 terms
OCHEM EXAM 3
Cytosine
Pyrimidine
Thymine
nucleotides
What amino acid is this?
What class is cytosine classified as?
What amino acid is this?
What are the building blocks of RNA and DNA?
Cytosine
What amino acid is this?
Pyrimidine
What class is cytosine classified as?
16 terms
ochem exam 3
HCl pKa
Sulphuric Acid H2SO4 pKa
Protonated alcohol/water pKa
Carboxylic acid pKa
-7
-5
-2
~4-5
HCl pKa
-7
Sulphuric Acid H2SO4 pKa
-5
39 terms
Ochem exam 3
-Cyclic... -conjugated (resonance)... -Flat…
Molecules that bond with a Hydrogen co…
O-H molecules
The more electronegative = The more so…
Aromatic compounds are:
What molecules can H-bond with water ?
What molecules can H-bond with water and itself?
How do you determine which molecule is most soluble in water?
-Cyclic... -conjugated (resonance)... -Flat…
Aromatic compounds are:
Molecules that bond with a Hydrogen co…
What molecules can H-bond with water ?
58 terms
OChem Test 3
good, good
good, good
good
good
Br- is a ___ nucleophile and a ___ leaving group
I- is a ___ nucleophile and a ___ leaving group
CH3S- is a ___ nucleophile
RS- is a ___ nucleophile
good, good
Br- is a ___ nucleophile and a ___ leaving group
good, good
I- is a ___ nucleophile and a ___ leaving group
14 terms
Ochem Lab- EXP 3
caffeine structure
what techniques will be used?
what is difficult about this process?
what ar the major components of tea le…
solid-liquid, and lie-liq extractions and sublimation (purifi…
complicated by the fact that the natural source (plant, anima…
cellulose, proteins, pigments, and tannins
caffeine structure
what techniques will be used?
solid-liquid, and lie-liq extractions and sublimation (purifi…
31 terms
OChem Ch 10.3
alkyl halide
PX3
H+, alkyl halide
alcohol
from alcohol to alkyl halide-no shift
from alcohol to alkyl halide-with shift
alkyl halide
PX3
from alcohol to alkyl halide-no shift
11 terms
Ochem Final-chapt. 3
Gauche conformer
Anti conformer
Alkyl halide
Ketone
Methyls close to eachother
Methyls on opposite eachother
Gauche conformer
Methyls close to eachother
Anti conformer
Methyls on opposite eachother
20 terms
OChem Quarter 3
Malonic ester
acetoacetic ester
toulene
Benzoate
Malonic ester
acetoacetic ester
16 terms
OCHEM Chapter 3- Bonding
Quantum numbers
Bonding orbitals
Antibonding orbitals
Single bonds
describe the size, shape, orientation, and number of atomic o…
created by head-to-head or tail-to-tail overlap of atomic orb…
created by head-to-head or tail-to-tail overlap of atomic orb…
-are sigma bonds... -contain two electrons
Quantum numbers
describe the size, shape, orientation, and number of atomic o…
Bonding orbitals
created by head-to-head or tail-to-tail overlap of atomic orb…
Ochem 3-4
Nucleophilicity
Electrophilicity
Leaving group tendency
Sn1 mechanism
the more negative, the better the nucleophile... -deprotonate to…
the more positive, the better the electrophile... -protonate to…
the weaker the base, the better the leaving group
-carbocation intermediate, 2 step... - 3° > 2° > 1° > CH₃... -polar…
Nucleophilicity
the more negative, the better the nucleophile... -deprotonate to…
Electrophilicity
the more positive, the better the electrophile... -protonate to…
41 terms
OChem Ch. 2 & 3
Stability of Conjugate Bases
Element Effects
Inductive Effects
Resonance Effects
I. Element Effects... II. Inductive Effects... III. Resonance Effec…
Acidity of HA increases as the electronegativity of A- increa…
Acidity of HA increases when we put electronegative atoms nea…
Delocalization of charage through resonance
Stability of Conjugate Bases
I. Element Effects... II. Inductive Effects... III. Resonance Effec…
Element Effects
Acidity of HA increases as the electronegativity of A- increa…
35 terms
BR OChem 3: Stereochemistry
configurational isomers
chirality
asymmetric/chiral carbons
enantiomers
have identical bonds but different spatial arrangement of atoms
a chiral molecule has at least 1 stereogenic center present.…
sp³ hybridized with 4 unique substituents attached
mirror images that are non-superimposable
configurational isomers
have identical bonds but different spatial arrangement of atoms
chirality
a chiral molecule has at least 1 stereogenic center present.…
13 terms
OCHEM Chapter 3
principal quantum number
azimuthal quantum number
magnetic quantum number
spin quantum number
First quantum number, designated as the letter "n." It takes…
Second quantum number, designated by the letter "l." This "an…
The third quantum number, designated by m_l, it describes a p…
The quantum number that has only two possible values, +1/2 an…
principal quantum number
First quantum number, designated as the letter "n." It takes…
azimuthal quantum number
Second quantum number, designated by the letter "l." This "an…
26 terms
ochem t3
acetone
acetone
N,N-Dimethylformamide (DNAF)
Acetonitrile (MeCN)
polar aprotic
polar aprotic
polar aprotic
acetone
acetone
polar aprotic
OChem Unit 3
Hydrohalogenation
Radical Hydrohalogenation
Acid-catalyzed Hydration
Oxymercuration-demercuration
Carbocation... Markovnikov... Product: Alkyl Halides... HX
Only with HBr and ROOR... Anti-Mark
Carbocations... Markovnikov... Product: Alcohol... H2O and HA... Double b…
Bridged ion... Markovnikov... Anti (trans products)... Product: Alcoho…
Hydrohalogenation
Carbocation... Markovnikov... Product: Alkyl Halides... HX
Radical Hydrohalogenation
Only with HBr and ROOR... Anti-Mark
92 terms
Ochem EV 3
why is benzene a unique model for arom…
what type of reaction does benzene und…
some common names of benzenes?
benzenze is very stable/. What can be…
-planar... -sp2... -*six P orbitals are parallel and perpendicular…
EAS (electrophilic substitution)
-look at other file
-KMnO4... -K2Cr2O7... -yield is one carboxyl group for each att…
why is benzene a unique model for arom…
-planar... -sp2... -*six P orbitals are parallel and perpendicular…
what type of reaction does benzene und…
EAS (electrophilic substitution)
26 terms
Ochem 3 test
Addition of HX
Acid-Catalyzed Hydration
Addition of Bromine and Chlorine
Addition of HOCl and HBr
-alkenes to haloalkanes ... -electrophilic addition reaction... -Ma…
-alkene to alcohol ... -Markovnikov regioselectivity ... -not stere…
-alkene to vicinal dihalide ... -bridged halonium ion intermedia…
-alkenes to halohyrdins... -Markovnikov regioselectivity in the-…
Addition of HX
-alkenes to haloalkanes ... -electrophilic addition reaction... -Ma…
Acid-Catalyzed Hydration
-alkene to alcohol ... -Markovnikov regioselectivity ... -not stere…
81 terms
OCHEM test #3
If you want to turn a secondary OH int…
If you want to turn a primary OH into…
During oxidation of alcohols to aldehy…
How many oxidation reactions will a pr…
KMnO4, CrO3 and H+, NA2Cr2O7
KMnO4, CrO3 and H+, NA2Cr2O7
PCC
two, aldehyde, carboxylic acid
If you want to turn a secondary OH int…
KMnO4, CrO3 and H+, NA2Cr2O7
If you want to turn a primary OH into…
KMnO4, CrO3 and H+, NA2Cr2O7
46 terms
Ochem Ch 3
functional group
pi bond
nucleophile
ethane
atom or group of atoms with characteristic chemical and physi…
common in c-c and c-o double bonds; easily broken in chem rea…
a chemical species that donates an electron pair to an electr…
CH3CH3; only sigma bonds, no functional group; no polar bonds…
functional group
atom or group of atoms with characteristic chemical and physi…
pi bond
common in c-c and c-o double bonds; easily broken in chem rea…
19 terms
Chapter 1 &3 ochem
A pie bond makes a molecule a what?
A nucleophil is what? Has a what charge?
Electrophil is what?
Alkane(hydrocarbon)
Base and nucleophil
negative.. Seeking nucleus of other atoms; BASE
a positive charge
r-h example ch3 -ch3 linear
A pie bond makes a molecule a what?
Base and nucleophil
A nucleophil is what? Has a what charge?
negative.. Seeking nucleus of other atoms; BASE
31 terms
Ochem ch3
The most important result of ring inve…
cis
trans
Stereoisomers
is that any substituent that is axial in the original chair c…
Substitutes on same side
substitutes on diff sides
atoms bonded in the same order—that is, they have the same co…
The most important result of ring inve…
is that any substituent that is axial in the original chair c…
cis
Substitutes on same side
55 terms
Ochem Ch 3
alkanes
hydrocarbons
straight-chain alkanes
constitutional isomers
composed of only carbon atoms and hydrogen atoms and contain…
compounds that contain only carbon and hydrogen; alkanes are…
alkanes in which the carbons form a continuous chain with no…
compounds such as butane and isobutane that have the same mol…
alkanes
composed of only carbon atoms and hydrogen atoms and contain…
hydrocarbons
compounds that contain only carbon and hydrogen; alkanes are…
12 terms
Ch. 3 and 4 OCHEM
What are the 4 major reaction categori…
Bronstead Lowery Acid (think protons)
Bronstead Lowery Base
Lewis Acid Base Theory: Lewis Acid (th…
1. Substitutions... 2. Additions... 3. Elimination... 4. Rearrangements
Proton donor
Proton Acceptor
acids are electron pair acceptors
What are the 4 major reaction categori…
1. Substitutions... 2. Additions... 3. Elimination... 4. Rearrangements
Bronstead Lowery Acid (think protons)
Proton donor
17 terms
OChem Exam 3
H2O ... H+
1. H2O, Hg(OAc)2... 2. NaBH4
1. BH3... 2. HOOH, NaOH
HX... X=Cl,Br, or I
OH on more substituted carbon... H on less substituted carbon... *b…
OH on more substituted carbon
OH on less substituted carbon... H on more sub.... *syn addition
X on more substituted Carbon... *beware carbocation rearrangemen…
H2O ... H+
OH on more substituted carbon... H on less substituted carbon... *b…
1. H2O, Hg(OAc)2... 2. NaBH4
OH on more substituted carbon
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