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MCAT > O Chem Reactions > Flashcards

O Chem Reactions Flashcards

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MCAT flashcards
1
Q

HYDROGENATION

A
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2
Q

HYDROHALOGENATION

A
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3
Q

HALOGENATION

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4
Q

HALOHYDRIN FORMATION

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5
Q

ACID CATALYZED HYDRATION

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6
Q

OXYMERCURATION REDUCTION

A
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7
Q

ALKOXYMERCURATION REDUCTION

A
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8
Q

HYDROBORATION OXIDATION

A
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9
Q

EPOXIDATION

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10
Q

DIHYDROXYLATION

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11
Q

OXIDATIVE CLEAVAGE

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12
Q

OZONOLYSIS

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13
Q

CYCLOPROPONATION

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14
Q

ALKYNE REDUCTION

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15
Q

HYDRATION

A
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16
Q

ALKYNE HYDROHALOGENATION

A
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17
Q

ALKYNE HYDROGENATION

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18
Q

ALKYNE OZONOLYSIS

A
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19
Q

ALKYNE PERMANGANATE OXIDATION

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20
Q

ALKYNE FORMATION

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21
Q

ALKYNE CHAIN ELONGATION

A
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22
Q

ALKANE TO ALKYL HALIDE

A
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23
Q

ALKENE BROMINATION (ELECTROPHILIC ADDITION)

A
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24
Q

ALKENE TO ALKYL BROMIDE (WITH PEROXIDE)

A

BROMINATION VIA ANTI-MARK.

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25
Q

ELIMINATION REACTION (tBuO-)

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26
Q

WILLIAMSON ETHER SYNTHESIS (STEP 1)

A
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27
Q

ALCOHOL + HCl

A
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28
Q

ALCOHOL + PBr3

A
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29
Q

ALCOHOL + SOCl2/NH3

A

HYDROGENATION

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30
Q

DEHYDRATION H2SO4

A
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31
Q

ALCOHOL + RSO2Cl

A
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32
Q

SULFONATE NUCLEOPHILIC SUBSTITUTION

A
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33
Q

ALCOHOL + H2SO4

A

OXIDATION TERTIARY ALCOHOL TO KETONE

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34
Q

JONES OXIDATION

A
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35
Q

ALCOHOL + PCC

A

OXIDATION ALCOHOL TO ALDEHYDE

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36
Q

ALKOXIDE ETHER SYNTHESIS

A
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37
Q

EPOXIDATION

A
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38
Q

BASE CATALYZED EPOXIDE RING OPENING

A
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39
Q

OZONOLYSIS

A
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40
Q

GRIGNARD REACTION

A
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41
Q

DIES-ALDER REACTION

A
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42
Q

ALDOL REACTION

A
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43
Q

ELIMINATION

A
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44
Q

FREE-RADICAL HALOGENATION

A
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45
Q

HYRDROGENATION

A
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46
Q

ELECTROPHILIC AROMATIC SUBSTITUTION

A
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47
Q

FISHER ESTERIFICATION

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48
Q

SUBSTITUTION

A
49
Q

WILLIAMSON ETHER SYNTHESIS (STEP 2)

A
50
Q

TERTIARY ALCOHOL H2SO4

A

E1 ALCOHOL TO ALKENE

51
Q

IF GIVEN AN ALKENE, X2, AND H20, WHAT IS FORMED?

A

HALOHYDRIN (R-OH-C-X)

52
Q

IF GIVEN AN ALKENE, X2, AND ROH, WHAT IS FORMED?

A

ETHER

53
Q

IF GIVEN AN ALKENE, H2SO4, AND H20, WHAT IS FORMED?

A

AN ALCOHOL (ATTACHES TO ALPHA H)

54
Q

IF GIVEN AN ALKENE, H2SO4, AND ROH, WHAT IS FORMED?

A

ETHER (WHERE ALPHA H WAS)

55
Q

ALKENE + H2/Pt GIVES WHAT?

A

HYDROGENATION: ALKANE VIA SYN ADDITION

56
Q

ALKENE + HX/CCl4 GIVES WHAT?

A

HYDROHALOGENATION: ALKYL HALIDE, X TAKES PLACE OF ALPHA H

57
Q

ALKENE + HBR + ROOR GIVES WHAT?

A

HYDROHALOGENATION: ALKYL BROMIDE (PRIMARY)

58
Q

ALKENE + X2 + CCl4 GIVES WHAT?

A

HALOGENATION: ALKYL HALIDE VIA ANTI-ADDITION (2 X, ANTI)

59
Q

ALKENE + 1. HG(OAc)2 H2O 2. NaBH4 GIVES WHAT?

A

OXYMERCURATION-REDUCTION OF ALCOHOL (SECNONDARY)

60
Q

ALKENE + 1. Hg(OAc)2, ROH 2. NaBH4 GIVES WHAT?

A

ALKOXYMERCURATION-REDUCTION ALKOXIDE VIA ANTI ADDITION (SECONDARY)

61
Q

ALKENE + BH3, THF AND NaOH, H2O GIVES WHAT?

A

HYDROBORATION-OXIDATION PRIMARY ALCOHOL

62
Q

ALKENE + PERACID (RCOOOH) GIVES WHAT?

A

EPOXIDE VIA SYN

63
Q

mCPBA IS OFTEN USED FOR WHAT?

A

EPOXIDATION

64
Q

ALKENE + OsO4 GIVES WHAT?

A

DIHYDROXYLATION: DOUBLE ALCOHOL VIA SYN ADDITION

65
Q

ALKENE + KMnO4, cold/dilute GIVES WHAT?

A

DIHYDROXYLATION: DOUBLE ALCOHOL VIA SYN ADDITION

66
Q

ALKENE + mCPBA/H3O+ GIVES WHAT?

A

DIHYDROXYLATION: DOUBLE ALCOHOL VIA ANTI ADDITION

67
Q

ALKENE + KMnO4, HOT GIVES WHAT?

A

OXIDATIVE CLEAVAGE (2 CARBOXYLIC ACIDS FORM ON DOUBLE BOND)

68
Q

ALKENE + O3, (CH3)2S GIVES WHAT?

A

OZONOLYSIS: PRIMARY CARBON ON DOUBLE BOND GIVES 2 ALHDEHYDES

69
Q

ALKENE + O3, H2O2 GIVES WHAT?

A

OZONOLYSIS: PRIMARY CARBON BECOMES 2 CARBOXYLIC ACIDS

70
Q

WHAT IS THE SIMMONS-SMITH REACTION?

A

CYCLOPROPONATION:

ALKENE + CH2I2, Zn(Cu) = RING ALONG DOUBLE BOND

ALKENE + CHX3, NAOH/H2O = RING ALONG DOUBLE BOND WITH DOUBLE HALIDE

71
Q

H2 AND Pd OR Pt DO WHAT TO AN ALKYNE?

A

FULL REDUCTION TO ALKANE

72
Q

Na and NH3 DO WHAT TO AN ALKYNE?

A

PARTIAL REDUCTION TO TRANS-ALKENE

73
Q

H2 AND LINDLAR’S CATALYST DO WHAT TO AN ALKYNE?

A

PARTIAL REDUCTION TO CIS-ALKENE

74
Q

HgSO4, H2SO4, H2O DO WHAT TO AN ALKYNE?

A

HYDRATION OF ALKYNE TO SECONDARY ENOL (OH ON DOUBLE BOND)

75
Q

BH3, THF, H2O2, OH DOE WHAT TO AN ALKYNE?

A

HYDRATION TO PRIMARY ENOL (ALCOHOL ON DOUBLE BOND)

76
Q

KETO-ENOL TAUTOMERAIZATION DOES WHAT TO A SECONDARY ENOL?

A

PRODUCES A KETONE

77
Q

KETO-ENOL TAUTOMERAIZATION DOES WHAT TO A PRIMARY ENOL?

A

PRODUCES AN ALDEHYDE

78
Q

EXCESS HX DOES WHAT TO AN ALKYNE?

A

HYDROHALOGENATION TO PRODUCE AN ALKYL HALIDE (2 X ON ONE C)

79
Q

Br2 IN EXCESS DOES WHAT TO AN ALKYNE?

A

HALOGENATION: PRODUCES A QUADRUPLE ALKYL BROMIDE (2 Br ON EACH C ON EACH SIDE OF THE TRIPLE BOND)

80
Q

O3 AND H2O DO WHAT TO A SECONDARY ALKYNE?

A

OZONOLYSIS: PRODUCES 2 CARBOXYLIC ACIDS ALONG TRIPLE BOND

81
Q

O3 AND H20 DO WHAT TO A PRIMARY ALKYNE?

A

OZONOLYSIS: PRODUCE ONE CARBOXYLIC ACID AND CO2 GAS

82
Q

KMnO4 AND H2O DO WHAT TO AN ALKYNE?

A

PERMANGANATE OXIDATION: PRODUCES TWO KETONES ALONG TRIPLE BOND

83
Q

KMnO4, OH-, HEAT (BASIC) DO WHAT TO AN ALKYNE?

A

PERMANGANATE OXIDATION: PRODUCE TWO CARBOXYLATE ANIONS (RCOO-) TO THEN FURTHER BECOME CARBOXYLIC ACIDS WITH THE ADDITION OF H3O+

84
Q

HOW DO YOU CREATE AN ALKYNE FROM AN ALKYL BROMIDE?

A

ADD NaNH2 (2 EQUIV.), NH3 FOR DOUBLE ELIMINATION

85
Q

WHAT REAGENTS ARE NEEDED FOR AROMATIC HALOGENATION?

A

Br2, FeBr3 (OR Cl2, AlCl3)

86
Q

WHAT REAGENTS ARE NEEDED FOR AROMATIC NITRATION?

A

HNO3, H2SO4

87
Q

WHAT REAGENTS ARE NEEDED FOR AROMATIC SULFONATION?

A

SO3, H2SO4

88
Q

DESCRIBE FRIEDEL-CRAFTS ALKYLATION AND THE REAGENTS NEEDED

A

BENZENE RING, WITH R-Cl, AlCl3 PRODUCE R GROUP ATTACHED TO BENZENE

89
Q

DESCRIBE FRIEDEL-CRAFTS ACYLATION AND THE REAGENTS NEEDED

A

BENZENE RING, WITH ACYL CHLORIDE (R, CARBONYL, CL) FORM BENZENE/KETONE

90
Q

DESCRIBE ORTHO, META, AND PARA SUBSTITUTION ON A BENZENE RING

A
91
Q

PRIMARY ALCOHOL + PCC GIVES…?

A

ALDEHYDE (WEAK OX. AGENT)

92
Q

PRIMARY ALCOHOL WITH CrO3, H3O+ GIVES…?

A

CARBOXYLIC ACID (STRONG OX. AGENT)

93
Q

WHAT ARE THE 5 GROUPS OF STRONG OXIDIZING AGENTS?

A

CrO3/H3O+

H2CrO4

Na2Cr2O7/H2SO4

K2Cr2O7/H2SO4

KMnO4

94
Q

WHAT DOES A JONES REAGENT DO TO A PRIMARY ALCOHOL?

A

CARBOXYLIC ACID

95
Q

WHAT DOES A JONES REAGENT DO TO A SECONDARY ALCOHOL?

A

KETONE

96
Q

WHAT IS THE JONES REAGENT?

A

CrO3/H2SO4

97
Q

WHAT IS THE TOLLENS REAGENT USED FOR?

A

CONVERSION OF ALDEHYDE TO CARBOXYLIC ACID

98
Q

WHAT IS TOLLENS REAGENT?

A

AgNO3, NH3, H2O

99
Q

WHAT DOES OXIDATION OF BENZENE SIDE CHAINS ENTAIL?

A

USE OF KMnO4, ALL PRIMARY AND SECONDARY C GET OXIDIZED TO CARBOXYLIC ACIDS

**TERTIARY C ARE NOT REACTED

100
Q

WHAT IS THE BIRCH REDUCTION?

A

BENZENE + Li (or Na)/ROH, NH3, RESULTS IN PARA REDUCTION

101
Q

CARBOXYLIC ACID + LiAlH4 = ?

A

PRIMARY ALCOHOL (REDUCTION)

102
Q

ALDEHYDES + LiAlH4 (OR NaBH4, OR DIBAlH) = ?

A

REDUCTION: PRIMARY ALCOHOL

103
Q

KETONE + LiAlH4 (OR NaBH4, OR DIBAlH) = ?

A

REDUCTION: SECONDARY ALCOHOL

104
Q

ACETATE (R-COOR) + LiAlH4 = ?

A

PRIMARY ALCOHOL

105
Q

WHAT IS THE CLEMMENSON REACTION?

A

ACETOPHENONE (PHENYL-CARBONYL-R) + Zn(Hg)/HCl = PHENYL-ALKANE

106
Q

WHAT IS WOLFF-KISHNER REACTION?

A

ACETOPHENONE (PHENYL-CARBONYL-R) + H2NH2/ROH = PHENYL-ALKANE

107
Q

HOW IS AN ACID CHLORIDE CREATED?

A

CARBOXYLIC ACID + SOCl2

108
Q

HOW IS AN ESTER CREATED?

A

CARBOXYLIC ACID + ROH, H+ (ACID CATALYZED)

109
Q

HOW IS A THIOESTER CREATED?

A

CARBOXYLIC ACID + RSH

110
Q

HOW IS AN ACID ANHYDRIDE CREATED?

A

CARBOXYLIC ACID + ACID CHLORIDE, NaOH

111
Q

HOW IS AN AMIDE CREATED?

A

CARBOXYLIC ACID + R-NH-R, DCC

112
Q

HOW DO YOU SYNTHESIZE ALCOHOLS FROM ALKENES?

A

MARKOVNIKOV/ANTIMARK.

113
Q

HOW DO YOU SYNTHESIZE ALCOHOLS FROM ALKYL HALIDES?

A

SN1 OR SN2

114
Q

HOW DO YOU SYNTHESIZE ALCOHOLS FROM CARBONYL COMPOUNDS?

A

REDUCTION! NaBH4, LiAlH4, or grignard reagent

115
Q

WHAT IS NaBH4 SELECTIVE FOR?

A

ALDEHYDES AND KETONES, NO CARBOXYLIC ACIDS OR ESTERS

116
Q

WHAT IS LiAlBH4 SELECTIVE FOR?

A

CARBOXYLIC ACIDS AND ESTERS

117
Q

WHAT IS THE DIFFERENCE BETWEEN JONES AND PCC?

A

FOR PRIMARY ALCOHOLS: JONES OXIDIZES ALCOHOL ALL THE WAY TO CARBOXYLIC ACID, PCC OXIDIZES ALCOHOL TO ALDEHYDE

118
Q

TRUE OR FALSE: TERTIARY ALCHOLS CAN BE OXIDIZED TO KETONES

A

FALSE, TERTIARY ALCHOLS CANNOT BE OXIDIZED BECAUSE THEY DO NOT HAVE AN ALPHA HYDROGEN

119
Q

WHICH IS MORE LIKELY: NUCLEOPHILIC ATTACK ON ALDEHYDE OR KETONE?

A

MORE LIKELY ON ALDEHYDE BECAUSE LESS STABILITY AND LESS STERIC HINDRANCE

MCAT (17 decks)

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