O Chem Reactions Flashcards
HYDROGENATION
HYDROHALOGENATION
HALOGENATION
HALOHYDRIN FORMATION
ACID CATALYZED HYDRATION
OXYMERCURATION REDUCTION
ALKOXYMERCURATION REDUCTION
HYDROBORATION OXIDATION
EPOXIDATION
DIHYDROXYLATION
OXIDATIVE CLEAVAGE
OZONOLYSIS
CYCLOPROPONATION
ALKYNE REDUCTION
HYDRATION
ALKYNE HYDROHALOGENATION
ALKYNE HYDROGENATION
ALKYNE OZONOLYSIS
ALKYNE PERMANGANATE OXIDATION
ALKYNE FORMATION
ALKYNE CHAIN ELONGATION
ALKANE TO ALKYL HALIDE
ALKENE BROMINATION (ELECTROPHILIC ADDITION)
ALKENE TO ALKYL BROMIDE (WITH PEROXIDE)
BROMINATION VIA ANTI-MARK.
ELIMINATION REACTION (tBuO-)
WILLIAMSON ETHER SYNTHESIS (STEP 1)
ALCOHOL + HCl
ALCOHOL + PBr3
ALCOHOL + SOCl2/NH3
HYDROGENATION
DEHYDRATION H2SO4
ALCOHOL + RSO2Cl
SULFONATE NUCLEOPHILIC SUBSTITUTION
ALCOHOL + H2SO4
OXIDATION TERTIARY ALCOHOL TO KETONE
JONES OXIDATION
ALCOHOL + PCC
OXIDATION ALCOHOL TO ALDEHYDE
ALKOXIDE ETHER SYNTHESIS
EPOXIDATION
BASE CATALYZED EPOXIDE RING OPENING
OZONOLYSIS
GRIGNARD REACTION
DIES-ALDER REACTION
ALDOL REACTION
ELIMINATION
FREE-RADICAL HALOGENATION
HYRDROGENATION
ELECTROPHILIC AROMATIC SUBSTITUTION
FISHER ESTERIFICATION
SUBSTITUTION
WILLIAMSON ETHER SYNTHESIS (STEP 2)
TERTIARY ALCOHOL H2SO4
E1 ALCOHOL TO ALKENE
IF GIVEN AN ALKENE, X2, AND H20, WHAT IS FORMED?
HALOHYDRIN (R-OH-C-X)
IF GIVEN AN ALKENE, X2, AND ROH, WHAT IS FORMED?
ETHER
IF GIVEN AN ALKENE, H2SO4, AND H20, WHAT IS FORMED?
AN ALCOHOL (ATTACHES TO ALPHA H)
IF GIVEN AN ALKENE, H2SO4, AND ROH, WHAT IS FORMED?
ETHER (WHERE ALPHA H WAS)
ALKENE + H2/Pt GIVES WHAT?
HYDROGENATION: ALKANE VIA SYN ADDITION
ALKENE + HX/CCl4 GIVES WHAT?
HYDROHALOGENATION: ALKYL HALIDE, X TAKES PLACE OF ALPHA H
ALKENE + HBR + ROOR GIVES WHAT?
HYDROHALOGENATION: ALKYL BROMIDE (PRIMARY)
ALKENE + X2 + CCl4 GIVES WHAT?
HALOGENATION: ALKYL HALIDE VIA ANTI-ADDITION (2 X, ANTI)
ALKENE + 1. HG(OAc)2 H2O 2. NaBH4 GIVES WHAT?
OXYMERCURATION-REDUCTION OF ALCOHOL (SECNONDARY)
ALKENE + 1. Hg(OAc)2, ROH 2. NaBH4 GIVES WHAT?
ALKOXYMERCURATION-REDUCTION ALKOXIDE VIA ANTI ADDITION (SECONDARY)
ALKENE + BH3, THF AND NaOH, H2O GIVES WHAT?
HYDROBORATION-OXIDATION PRIMARY ALCOHOL
ALKENE + PERACID (RCOOOH) GIVES WHAT?
EPOXIDE VIA SYN
mCPBA IS OFTEN USED FOR WHAT?
EPOXIDATION
ALKENE + OsO4 GIVES WHAT?
DIHYDROXYLATION: DOUBLE ALCOHOL VIA SYN ADDITION
ALKENE + KMnO4, cold/dilute GIVES WHAT?
DIHYDROXYLATION: DOUBLE ALCOHOL VIA SYN ADDITION
ALKENE + mCPBA/H3O+ GIVES WHAT?
DIHYDROXYLATION: DOUBLE ALCOHOL VIA ANTI ADDITION
ALKENE + KMnO4, HOT GIVES WHAT?
OXIDATIVE CLEAVAGE (2 CARBOXYLIC ACIDS FORM ON DOUBLE BOND)
ALKENE + O3, (CH3)2S GIVES WHAT?
OZONOLYSIS: PRIMARY CARBON ON DOUBLE BOND GIVES 2 ALHDEHYDES
ALKENE + O3, H2O2 GIVES WHAT?
OZONOLYSIS: PRIMARY CARBON BECOMES 2 CARBOXYLIC ACIDS
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
H2 AND Pd OR Pt DO WHAT TO AN ALKYNE?
FULL REDUCTION TO ALKANE
Na and NH3 DO WHAT TO AN ALKYNE?
PARTIAL REDUCTION TO TRANS-ALKENE
H2 AND LINDLAR’S CATALYST DO WHAT TO AN ALKYNE?
PARTIAL REDUCTION TO CIS-ALKENE
HgSO4, H2SO4, H2O DO WHAT TO AN ALKYNE?
HYDRATION OF ALKYNE TO SECONDARY ENOL (OH ON DOUBLE BOND)
BH3, THF, H2O2, OH DOE WHAT TO AN ALKYNE?
HYDRATION TO PRIMARY ENOL (ALCOHOL ON DOUBLE BOND)
KETO-ENOL TAUTOMERAIZATION DOES WHAT TO A SECONDARY ENOL?
PRODUCES A KETONE
KETO-ENOL TAUTOMERAIZATION DOES WHAT TO A PRIMARY ENOL?
PRODUCES AN ALDEHYDE
EXCESS HX DOES WHAT TO AN ALKYNE?
HYDROHALOGENATION TO PRODUCE AN ALKYL HALIDE (2 X ON ONE C)
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)
O3 AND H2O DO WHAT TO A SECONDARY ALKYNE?
OZONOLYSIS: PRODUCES 2 CARBOXYLIC ACIDS ALONG TRIPLE BOND
O3 AND H20 DO WHAT TO A PRIMARY ALKYNE?
OZONOLYSIS: PRODUCE ONE CARBOXYLIC ACID AND CO2 GAS
KMnO4 AND H2O DO WHAT TO AN ALKYNE?
PERMANGANATE OXIDATION: PRODUCES TWO KETONES ALONG TRIPLE BOND
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+
HOW DO YOU CREATE AN ALKYNE FROM AN ALKYL BROMIDE?
ADD NaNH2 (2 EQUIV.), NH3 FOR DOUBLE ELIMINATION
WHAT REAGENTS ARE NEEDED FOR AROMATIC HALOGENATION?
Br2, FeBr3 (OR Cl2, AlCl3)
WHAT REAGENTS ARE NEEDED FOR AROMATIC NITRATION?
HNO3, H2SO4
WHAT REAGENTS ARE NEEDED FOR AROMATIC SULFONATION?
SO3, H2SO4
DESCRIBE FRIEDEL-CRAFTS ALKYLATION AND THE REAGENTS NEEDED
BENZENE RING, WITH R-Cl, AlCl3 PRODUCE R GROUP ATTACHED TO BENZENE
DESCRIBE FRIEDEL-CRAFTS ACYLATION AND THE REAGENTS NEEDED
BENZENE RING, WITH ACYL CHLORIDE (R, CARBONYL, CL) FORM BENZENE/KETONE
DESCRIBE ORTHO, META, AND PARA SUBSTITUTION ON A BENZENE RING
PRIMARY ALCOHOL + PCC GIVES…?
ALDEHYDE (WEAK OX. AGENT)
PRIMARY ALCOHOL WITH CrO3, H3O+ GIVES…?
CARBOXYLIC ACID (STRONG OX. AGENT)
WHAT ARE THE 5 GROUPS OF STRONG OXIDIZING AGENTS?
CrO3/H3O+
H2CrO4
Na2Cr2O7/H2SO4
K2Cr2O7/H2SO4
KMnO4
WHAT DOES A JONES REAGENT DO TO A PRIMARY ALCOHOL?
CARBOXYLIC ACID
WHAT DOES A JONES REAGENT DO TO A SECONDARY ALCOHOL?
KETONE
WHAT IS THE JONES REAGENT?
CrO3/H2SO4
WHAT IS THE TOLLENS REAGENT USED FOR?
CONVERSION OF ALDEHYDE TO CARBOXYLIC ACID
WHAT IS TOLLENS REAGENT?
AgNO3, NH3, H2O
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
WHAT IS THE BIRCH REDUCTION?
BENZENE + Li (or Na)/ROH, NH3, RESULTS IN PARA REDUCTION
CARBOXYLIC ACID + LiAlH4 = ?
PRIMARY ALCOHOL (REDUCTION)
ALDEHYDES + LiAlH4 (OR NaBH4, OR DIBAlH) = ?
REDUCTION: PRIMARY ALCOHOL
KETONE + LiAlH4 (OR NaBH4, OR DIBAlH) = ?
REDUCTION: SECONDARY ALCOHOL
ACETATE (R-COOR) + LiAlH4 = ?
PRIMARY ALCOHOL
WHAT IS THE CLEMMENSON REACTION?
ACETOPHENONE (PHENYL-CARBONYL-R) + Zn(Hg)/HCl = PHENYL-ALKANE
WHAT IS WOLFF-KISHNER REACTION?
ACETOPHENONE (PHENYL-CARBONYL-R) + H2NH2/ROH = PHENYL-ALKANE
HOW IS AN ACID CHLORIDE CREATED?
CARBOXYLIC ACID + SOCl2
HOW IS AN ESTER CREATED?
CARBOXYLIC ACID + ROH, H+ (ACID CATALYZED)
HOW IS A THIOESTER CREATED?
CARBOXYLIC ACID + RSH
HOW IS AN ACID ANHYDRIDE CREATED?
CARBOXYLIC ACID + ACID CHLORIDE, NaOH
HOW IS AN AMIDE CREATED?
CARBOXYLIC ACID + R-NH-R, DCC
HOW DO YOU SYNTHESIZE ALCOHOLS FROM ALKENES?
MARKOVNIKOV/ANTIMARK.
HOW DO YOU SYNTHESIZE ALCOHOLS FROM ALKYL HALIDES?
SN1 OR SN2
HOW DO YOU SYNTHESIZE ALCOHOLS FROM CARBONYL COMPOUNDS?
REDUCTION! NaBH4, LiAlH4, or grignard reagent
WHAT IS NaBH4 SELECTIVE FOR?
ALDEHYDES AND KETONES, NO CARBOXYLIC ACIDS OR ESTERS
WHAT IS LiAlBH4 SELECTIVE FOR?
CARBOXYLIC ACIDS AND ESTERS
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
TRUE OR FALSE: TERTIARY ALCHOLS CAN BE OXIDIZED TO KETONES
FALSE, TERTIARY ALCHOLS CANNOT BE OXIDIZED BECAUSE THEY DO NOT HAVE AN ALPHA HYDROGEN
WHICH IS MORE LIKELY: NUCLEOPHILIC ATTACK ON ALDEHYDE OR KETONE?
MORE LIKELY ON ALDEHYDE BECAUSE LESS STABILITY AND LESS STERIC HINDRANCE
