1
Q
HYDROGENATION
A
2
Q
HYDROHALOGENATION
A
3
Q
HALOGENATION
A
4
Q
HALOHYDRIN FORMATION
A
5
Q
ACID CATALYZED HYDRATION
A
6
Q
OXYMERCURATION REDUCTION
A
7
Q
ALKOXYMERCURATION REDUCTION
A
8
Q
HYDROBORATION OXIDATION
A
9
Q
EPOXIDATION
A
10
Q
DIHYDROXYLATION
A
11
Q
OXIDATIVE CLEAVAGE
A
12
Q
OZONOLYSIS
A
13
Q
CYCLOPROPONATION
A
14
Q
ALKYNE REDUCTION
A
15
Q
HYDRATION
A
16
Q
ALKYNE HYDROHALOGENATION
A
17
Q
ALKYNE HYDROGENATION
A
18
Q
ALKYNE OZONOLYSIS
A
19
Q
ALKYNE PERMANGANATE OXIDATION
A
20
Q
ALKYNE FORMATION
A
21
Q
ALKYNE CHAIN ELONGATION
A
22
Q
ALKANE TO ALKYL HALIDE
A
23
Q
ALKENE BROMINATION (ELECTROPHILIC ADDITION)
A
24
Q
ALKENE TO ALKYL BROMIDE (WITH PEROXIDE)
A
BROMINATION VIA ANTI-MARK.
25
ELIMINATION REACTION (tBuO-)
26
WILLIAMSON ETHER SYNTHESIS (STEP 1)
27
ALCOHOL + HCl
28
ALCOHOL + PBr3
29
ALCOHOL + SOCl2/NH3
HYDROGENATION
30
DEHYDRATION H2SO4
31
ALCOHOL + RSO2Cl
32
SULFONATE NUCLEOPHILIC SUBSTITUTION
33
ALCOHOL + H2SO4
OXIDATION TERTIARY ALCOHOL TO KETONE
34
JONES OXIDATION
35
ALCOHOL + PCC
OXIDATION ALCOHOL TO ALDEHYDE
36
ALKOXIDE ETHER SYNTHESIS
37
EPOXIDATION
38
BASE CATALYZED EPOXIDE RING OPENING
39
OZONOLYSIS
40
GRIGNARD REACTION
41
DIES-ALDER REACTION
42
ALDOL REACTION
43
ELIMINATION
44
FREE-RADICAL HALOGENATION
45
HYRDROGENATION
46
ELECTROPHILIC AROMATIC SUBSTITUTION
47
FISHER ESTERIFICATION
48
SUBSTITUTION
49
WILLIAMSON ETHER SYNTHESIS (STEP 2)
50
TERTIARY ALCOHOL H2SO4
E1 ALCOHOL TO ALKENE
51
IF GIVEN AN ALKENE, X2, AND H20, WHAT IS FORMED?
HALOHYDRIN (R-OH-C-X)
52
IF GIVEN AN ALKENE, X2, AND ROH, WHAT IS FORMED?
ETHER
53
IF GIVEN AN ALKENE, H2SO4, AND H20, WHAT IS FORMED?
AN ALCOHOL (ATTACHES TO ALPHA H)
54
IF GIVEN AN ALKENE, H2SO4, AND ROH, WHAT IS FORMED?
ETHER (WHERE ALPHA H WAS)
55
ALKENE + H2/Pt GIVES WHAT?
HYDROGENATION: ALKANE VIA SYN ADDITION
56
ALKENE + HX/CCl4 GIVES WHAT?
HYDROHALOGENATION: ALKYL HALIDE, X TAKES PLACE OF ALPHA H
57
ALKENE + HBR + ROOR GIVES WHAT?
HYDROHALOGENATION: ALKYL BROMIDE (PRIMARY)
58
ALKENE + X2 + CCl4 GIVES WHAT?
HALOGENATION: ALKYL HALIDE VIA ANTI-ADDITION (2 X, ANTI)
59
ALKENE + 1. HG(OAc)2 H2O 2. NaBH4 GIVES WHAT?
OXYMERCURATION-REDUCTION OF ALCOHOL (SECNONDARY)
60
ALKENE + 1. Hg(OAc)2, ROH 2. NaBH4 GIVES WHAT?
ALKOXYMERCURATION-REDUCTION ALKOXIDE VIA ANTI ADDITION (SECONDARY)
61
ALKENE + BH3, THF AND NaOH, H2O GIVES WHAT?
HYDROBORATION-OXIDATION PRIMARY ALCOHOL
62
ALKENE + PERACID (RCOOOH) GIVES WHAT?
EPOXIDE VIA SYN
63
mCPBA IS OFTEN USED FOR WHAT?
EPOXIDATION
64
ALKENE + OsO4 GIVES WHAT?
DIHYDROXYLATION: DOUBLE ALCOHOL VIA SYN ADDITION
65
ALKENE + KMnO4, cold/dilute GIVES WHAT?
DIHYDROXYLATION: DOUBLE ALCOHOL VIA SYN ADDITION
66
ALKENE + mCPBA/H3O+ GIVES WHAT?
DIHYDROXYLATION: DOUBLE ALCOHOL VIA ANTI ADDITION
67
ALKENE + KMnO4, HOT GIVES WHAT?
OXIDATIVE CLEAVAGE (2 CARBOXYLIC ACIDS FORM ON DOUBLE BOND)
68
ALKENE + O3, (CH3)2S GIVES WHAT?
OZONOLYSIS: PRIMARY CARBON ON DOUBLE BOND GIVES 2 ALHDEHYDES
69
ALKENE + O3, H2O2 GIVES WHAT?
OZONOLYSIS: PRIMARY CARBON BECOMES 2 CARBOXYLIC ACIDS
70
WHAT IS THE SIMMONS-SMITH REACTION?
CYCLOPROPONATION:
ALKENE + CH2I2, Zn(Cu) = RING ALONG DOUBLE BOND
ALKENE + CHX3, NAOH/H2O = RING ALONG DOUBLE BOND WITH DOUBLE HALIDE
71
H2 AND Pd OR Pt DO WHAT TO AN ALKYNE?
FULL REDUCTION TO ALKANE
72
Na and NH3 DO WHAT TO AN ALKYNE?
PARTIAL REDUCTION TO TRANS-ALKENE
73
H2 AND LINDLAR'S CATALYST DO WHAT TO AN ALKYNE?
PARTIAL REDUCTION TO CIS-ALKENE
74
HgSO4, H2SO4, H2O DO WHAT TO AN ALKYNE?
HYDRATION OF ALKYNE TO SECONDARY ENOL (OH ON DOUBLE BOND)
75
BH3, THF, H2O2, OH DOE WHAT TO AN ALKYNE?
HYDRATION TO PRIMARY ENOL (ALCOHOL ON DOUBLE BOND)
76
KETO-ENOL TAUTOMERAIZATION DOES WHAT TO A SECONDARY ENOL?
PRODUCES A KETONE
77
KETO-ENOL TAUTOMERAIZATION DOES WHAT TO A PRIMARY ENOL?
PRODUCES AN ALDEHYDE
78
EXCESS HX DOES WHAT TO AN ALKYNE?
HYDROHALOGENATION TO PRODUCE AN ALKYL HALIDE (2 X ON ONE C)
79
Br2 IN EXCESS DOES WHAT TO AN ALKYNE?
HALOGENATION: PRODUCES A QUADRUPLE ALKYL BROMIDE (2 Br ON EACH C ON EACH SIDE OF THE TRIPLE BOND)
80
O3 AND H2O DO WHAT TO A SECONDARY ALKYNE?
OZONOLYSIS: PRODUCES 2 CARBOXYLIC ACIDS ALONG TRIPLE BOND
81
O3 AND H20 DO WHAT TO A PRIMARY ALKYNE?
OZONOLYSIS: PRODUCE ONE CARBOXYLIC ACID AND CO2 GAS
82
KMnO4 AND H2O DO WHAT TO AN ALKYNE?
PERMANGANATE OXIDATION: PRODUCES TWO KETONES ALONG TRIPLE BOND
83
KMnO4, OH-, HEAT (BASIC) DO WHAT TO AN ALKYNE?
PERMANGANATE OXIDATION: PRODUCE TWO CARBOXYLATE ANIONS (RCOO-) TO THEN FURTHER BECOME CARBOXYLIC ACIDS WITH THE ADDITION OF H3O+
84
HOW DO YOU CREATE AN ALKYNE FROM AN ALKYL BROMIDE?
ADD NaNH2 (2 EQUIV.), NH3 FOR DOUBLE ELIMINATION
85
WHAT REAGENTS ARE NEEDED FOR AROMATIC HALOGENATION?
Br2, FeBr3 (OR Cl2, AlCl3)
86
WHAT REAGENTS ARE NEEDED FOR AROMATIC NITRATION?
HNO3, H2SO4
87
WHAT REAGENTS ARE NEEDED FOR AROMATIC SULFONATION?
SO3, H2SO4
88
DESCRIBE FRIEDEL-CRAFTS ALKYLATION AND THE REAGENTS NEEDED
BENZENE RING, WITH R-Cl, AlCl3 PRODUCE R GROUP ATTACHED TO BENZENE
89
DESCRIBE FRIEDEL-CRAFTS ACYLATION AND THE REAGENTS NEEDED
BENZENE RING, WITH ACYL CHLORIDE (R, CARBONYL, CL) FORM BENZENE/KETONE
90
DESCRIBE ORTHO, META, AND PARA SUBSTITUTION ON A BENZENE RING
91
PRIMARY ALCOHOL + PCC GIVES...?
ALDEHYDE (WEAK OX. AGENT)
92
PRIMARY ALCOHOL WITH CrO3, H3O+ GIVES...?
CARBOXYLIC ACID (STRONG OX. AGENT)
93
WHAT ARE THE 5 GROUPS OF STRONG OXIDIZING AGENTS?
CrO3/H3O+
H2CrO4
Na2Cr2O7/H2SO4
K2Cr2O7/H2SO4
KMnO4
94
WHAT DOES A JONES REAGENT DO TO A PRIMARY ALCOHOL?
CARBOXYLIC ACID
95
WHAT DOES A JONES REAGENT DO TO A SECONDARY ALCOHOL?
KETONE
96
WHAT IS THE JONES REAGENT?
CrO3/H2SO4
97
WHAT IS THE TOLLENS REAGENT USED FOR?
CONVERSION OF ALDEHYDE TO CARBOXYLIC ACID
98
WHAT IS TOLLENS REAGENT?
AgNO3, NH3, H2O
99
WHAT DOES OXIDATION OF BENZENE SIDE CHAINS ENTAIL?
USE OF KMnO4, ALL PRIMARY AND SECONDARY C GET OXIDIZED TO CARBOXYLIC ACIDS
\*\*TERTIARY C ARE NOT REACTED
100
WHAT IS THE BIRCH REDUCTION?
BENZENE + Li (or Na)/ROH, NH3, RESULTS IN PARA REDUCTION
101
CARBOXYLIC ACID + LiAlH4 = ?
PRIMARY ALCOHOL (REDUCTION)
102
ALDEHYDES + LiAlH4 (OR NaBH4, OR DIBAlH) = ?
REDUCTION: PRIMARY ALCOHOL
103
KETONE + LiAlH4 (OR NaBH4, OR DIBAlH) = ?
REDUCTION: SECONDARY ALCOHOL
104
ACETATE (R-COOR) + LiAlH4 = ?
PRIMARY ALCOHOL
105
WHAT IS THE CLEMMENSON REACTION?
ACETOPHENONE (PHENYL-CARBONYL-R) + Zn(Hg)/HCl = PHENYL-ALKANE
106
WHAT IS WOLFF-KISHNER REACTION?
ACETOPHENONE (PHENYL-CARBONYL-R) + H2NH2/ROH = PHENYL-ALKANE
107
HOW IS AN ACID CHLORIDE CREATED?
CARBOXYLIC ACID + SOCl2
108
HOW IS AN ESTER CREATED?
CARBOXYLIC ACID + ROH, H+ (ACID CATALYZED)
109
HOW IS A THIOESTER CREATED?
CARBOXYLIC ACID + RSH
110
HOW IS AN ACID ANHYDRIDE CREATED?
CARBOXYLIC ACID + ACID CHLORIDE, NaOH
111
HOW IS AN AMIDE CREATED?
CARBOXYLIC ACID + R-NH-R, DCC
112
HOW DO YOU SYNTHESIZE ALCOHOLS FROM ALKENES?
MARKOVNIKOV/ANTIMARK.
113
HOW DO YOU SYNTHESIZE ALCOHOLS FROM ALKYL HALIDES?
SN1 OR SN2
114
HOW DO YOU SYNTHESIZE ALCOHOLS FROM CARBONYL COMPOUNDS?
REDUCTION! NaBH4, LiAlH4, or grignard reagent
115
WHAT IS NaBH4 SELECTIVE FOR?
ALDEHYDES AND KETONES, NO CARBOXYLIC ACIDS OR ESTERS
116
WHAT IS LiAlBH4 SELECTIVE FOR?
CARBOXYLIC ACIDS AND ESTERS
117
WHAT IS THE DIFFERENCE BETWEEN JONES AND PCC?
FOR PRIMARY ALCOHOLS: JONES OXIDIZES ALCOHOL ALL THE WAY TO CARBOXYLIC ACID, PCC OXIDIZES ALCOHOL TO ALDEHYDE
118
TRUE OR FALSE: TERTIARY ALCHOLS CAN BE OXIDIZED TO KETONES
FALSE, TERTIARY ALCHOLS CANNOT BE OXIDIZED BECAUSE THEY DO NOT HAVE AN ALPHA HYDROGEN
119
WHICH IS MORE LIKELY: NUCLEOPHILIC ATTACK ON ALDEHYDE OR KETONE?
MORE LIKELY ON ALDEHYDE BECAUSE LESS STABILITY AND LESS STERIC HINDRANCE
MCAT
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