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CHEM 8B: Quiz 3_Lievens
OChem
89
Organic Chemistry
Undergraduate 3
02/10/2018

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Cards

Term
[image]
COMMON NAME
Definition
toluene
Term
[image]
COMMON NAME
Definition
phenol
Term
[image]
COMMON NAME
Definition
anisole
Term
[image]
COMMON NAME
Definition
aniline
Term
[image]
ORIENTATION
Definition
meta
(1,3)
Term
[image]
ORIENTATION
Definition
para
(1,4)
Term
[image]
ORIENTATION
Definition
ortho
(1,2)
Term
[image]
COMMON NAME
Definition
benzoic acid
Term
[image]
COMMON NAME
Definition
styrene
Term
[image]
pKa
Definition
9.95
Term
[image]
pKa
Definition
7.5
Term
[image]
pKa
Definition
8.5
Term
[image]
pKa
Definition
9.38
Term
[image]
pKa
Definition
7.66
Term
[image]
pKa
Definition
10.70
Term
Naming Priority
Definition
1) Aldehyde
2) Ketone
3) Alcohol
4) Alkene/ Alkyne/ Benzene
5) Ether/ Alkane/ Haloalkane
Term
Class I Carbonyls
Definition
have leaving group
carboxylic acid derivative

Carbox Acid, Ester, Amide, Acylhalide
Term
Class II Carbonyls
Definition
no leaving group

Aldehyde, Ketone
Term
[image]
FUNCTIONAL GROUP
Definition
Carboxylic Acid
Term
[image]
FUNCTIONAL GROUP
Definition
Ester
Term
[image]
FUNCTIONAL GROUP
Definition
Amide
Term
[image]
FUNCTIONAL GROUP
Definition
Acylhalide
Term
[image]
Definition
Aldehyde
Term
[image]
COMMON NAME
Definition
Formaldehyde
Term
[image]
COMMON NAME
Definition
Acetylhalide
Term
[image]
COMMON NAME
Definition
Formyl
Term
[image]
COMMON NAME
Definition
Acetyl
Term
[image]
COMMON NAME
Definition
Acyl
Term
Single C Carbonyl on ring
Definition
Carbaldehyde
Term
Nomenclature: Aldehydes
Definition
*Aldehyde always C-1
*drop e- and -al
Term
Nomenclature: Ketones
Definition
*Drop -e, add -one
*=O x2 = -oxo group
Term
[image]
COMMON NAME
Definition
Acetone
Term
[image]
COMMON NAME
Definition
Ketone
Term
[image]
pKa
Definition
Aldehyde
16-18
Term
[image]
pKa
Definition
Ketone
19-21
Term
[image]
pKa
Definition
50
Term
[image]
pKa
Definition
44
Term
[image]
pKa
Definition
25
Term
[image]
pKa
Definition
16-18
Term
[image]
pKa
Definition
3-5
Term
[image]
pKa
Definition
16-18
Term
[image]
pKa
Definition
19-21
Term
[image]
pKa
Definition
25
Term
[image]
pKa
Definition
9
Term
[image]
pKa
Definition
11
Term
[image]
pKa
Definition
13
Term
Aromatics & pKa
Definition
Substituents affect pKa
Term
Electron Withdraw Substitution
Definition
*stabilize -
better acid
Term
Nu- Acyl Addition
Definition
*Major mechanism aldehydes and ketones
*Acid/ Base
Term
NAA Base
Definition
*Nu-
*Base catalysts
*anion
1)Nu- attack
2) protonation
Term
NAA Acid
Definition
Nu-H neutral
*acid catalst
*cation
H+ already present
1)Protonate
2) Nu- attack
Term
Organometallic Reagents
Definition
*Major new Nu- for carbonyls
*Gringard: Mg
*OrganoLi: 2Li, THF
Term
Formaldehyde + OM Rxns
Definition
1 alcohol
Term
Aldehyde + OM Rxns
Definition
2 alcohol
Term
Ketone + OM Rxns
Definition
3 alcohol
Term
Hydride Donor
Definition
*Nu-H
*Can make H-
*2 Types: LiAlH4, NaBH4
Term
Aldehyde + Hydride Donor
Definition
1 alcohol
Term
Ketone + Hydride Donor
Definition
2 alcohol
Term
NaBH4
Definition
*less reactive
*works with alcohol as H+ donor in place
Term
LiAlH4
Definition
*more reactive
*H3O+ after to add H+
Term
Cyanohydride
Definition
*Forms by Nu- Acyl Add to C=O w/ CN- or HCN
*Good way to add Nitrile to molecule
Term
Hydrogenation of Cyanohydride
Definition
*Add H2 to pi bond
Term
Hydrolysis of Cyanohydire
Definition
gives carboxylic acid
Term
Amine
Definition
*Good Nu-
Form
1) Imine- 1 amine
2) Enamine- 2 amine
Term
Enamine
Definition
*react with H2O to reform C=O
*reversible
Term
Connect Imine/Enamine to Amine
Definition
*Use reduction
*Pd/H2, NaBH3, CN(pH2)
Term
Geminal Diol
Definition
*product of H2O to C=O via Nuc Acyl Addn
*AKA hydration of carbonyl
*form from carbonyls in aq soln
*exist as equill, can't isolate
Term
% Geminal Diol
Definition
Better E+ attracts more H2O more inc %
Term
H2o Nu-
Definition
use ROH
*single addn with carbonyls
*hemiacetal
Term
Hemiacetal
Definition
any amount of ROH + conj base
Term
Cyclic hemiacetal
Definition
cyclic
can be isolated b/c solv not part of rxn
Term
Isolating acetals
Definition
*Neutralizing acid
* Freeze in place
*No reverse w/o H+
Term
Conjugated Carbonyls
Definition
2 electrophillic C
Term
Acetal: Strongly Basic Nu-
Definition
*tend to 1,2 addn
*react @ C=O
*pKa -25
*goes to largest part+, irreversible
*RMgBr, RLi, LiAlH4, NaBH4, C=C-
Term
Acetal: Weaker Nu-
Definition
*1,2 addn
*react @ B-Carb
*pKa- 25
*go to largest part+, reversible
Term
Inc donation
Definition
= inc pKa
Term
Low pKa
Definition
*good res struct
*low E
*stabalize -
Term
Improve pKa
Definition
add 2nd C=O
1,3 dicarbonyl
Term
Enolate Ions
Definition
*allow for tautomerization
*rearrangement
*equill between C+O + enol
*good Nu- w/ enols + Carbonyl
Term
Exception Enolate Ions
Definition
Phenol prefers enol b/c aromatic ring
Term
C=O + Nu-
Definition
Nucleophillic Acyl Addn
Term
C=O + Base + E+
(Base/ E+ or 1)base 2)E)
Definition
Enolatae Rxns
Term
Common E+
Definition
[image]
Term
Choices of New Group
Definition
E+: go to C
H+: go to O (taut)
Term
Add E+ to either side
Definition
when assymetric
Term
Thermodynamic Product
Definition
lots of time
weaker equillibrium base
NaOH
Term
Kinetic Product
Definition
faster
stronger base
NaH2, NaH on hindered base LDA
Term
Lithium Diisoprpyl Amide (LDA)
Definition
strong hindered base
means deprotanate
Term
Aldol Cond
Definition
carbonyl good E+
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