Reaction Table - Chem 2211

Tables of Reactions - Final Exam Version

Here are all the reactions you are responsible for and their locations in the text. I have 2 tables here - the first is arranged by the functional group of the product; the second is arranged by the functional group of the reactant. Reaction may appear two or more times. Reactions since Midterm #2 are in red.

Synthesis of Functional Groups

Carbon-Carbon bond forming reactions

Alkyne chain extension (section 6.10) R-CCNa + Br-R' ---> R-CC-R'
Grignard reaction (sections 12.7, 18.4) R-C(=O)-R' ---> R"RC(OH)-R' [carbonyl] R-C(=O)-O-R' ---> R"₂RC-OH + HO-R [carboxyl]	1. R"-MgBr; 2. H₃O⁺ 1. R"-MgBr; 2. H₃O⁺ [happens twice]
Wittig reaction (section 18.10) R₂C=O ---> R₂C=CHR'	Ph₃P=CHR', THF
Addition of cyanide to carbonyl (section 18.4) R₂C=O ---> R₂(OH)C-CN	CN^-, HCl

Synthesis of Alkanes

From alkenes and alkynes (sections 4.11, 6.8) R-CC-R ---> RH₂C-CH₂R	H₂, Pd/C
From carbonyls (section 18.6) R-C(=O)-R' ---> C-CH₂-R' [both aldehydes and ketones]	H₂NNH₂, OH^-, heat [Wolff-Kishner reaction]

Synthesis of Alkyl Halides

From alkanes (Section 9.2)
C_nH_2n+2 ---> C_nH_(2n+2)-yX_y
X₂, hv (X = Cl, Br) [NOTE: hv = light]

Addition of X₂ to alkenes and alkynes (sections 4.7, 6.5, Experiment 5)
R₂C=CR₂ ---> XR₂C-CR₂X

X₂ in CH₂Cl₂ (X = Cl, Br)

Addition of HX to alkene and alkyne - Markovnikov (sections 4.1, 6.5)
HRC=CR₂ ---> H₂RC-CR₂X
HX in ether (X = Cl, Br)
KI in H₃PO₄ (X = I)

Addition of HX to alkene, anti-Markovnikov (section 4.10)

HRC=CR₂ ---> HXRC-CR₂H

HBr with peroxide

Halohydrin reaction (section 4.7)
R₂C=CR₂ ---> (OR')R₂C-CR₂X
X₂ (X = Cl, Br) in water (R' = H) or an alcohol (R' = alkyl)

Allylic bromination (section 9.5)
R₂C=CR-CH₂-R ---> R₂C=CR-CHBr-R
NBS with peroxide

Conversion from alcohol (sections 12.1, 12.3, Experiment 6)
R₃C-OH ---> R₃C-X

HX in ether (X = Cl, Br, I, usually 3^o alcohols)
SOCl₂ in pyridine (X = Cl, 1^o or 2^o alcohols)
PBr₃ in ether (X = Br, 1^o or 2^o alcohols)

Cleavage of ethers (section 12.6)
R-O-R' ---> R-OH + R'-X
H-X in H₂O (X = Br, I)

Synthesis of Alkenes

Dehydration of alcohol (section 12.5, Experiment 4)
R₂HC-CR₂OH ---> R₂C=CR₂

H⁺ (aq), heat (e.g., H₂SO₄, H₂O, THF, 50^oC)
H⁺, THF, 25^oC (3^o alcohols)
POCl₃, pyridine, 0^oC (2^o, 3^o alcohols)

From alkyl halide (E1 or E2 reaction) (section 11.2)
R₂HC-CR₂X ---> R₂C=CR₂

OH^- (aq) or OH^- in ethanol
CH₃CH₂O^- in ethanol
LDA in ether

From alkyne (section 6.8)
R-CC-R ---> RHC=CHR (cis)
R-CC-R ---> RHC=CHR (trans)
H₂, Lindlar catalyst
Li (or Na), NH₃

From carbonyl (Wittig Reaction) (section 18.10)
R₂C=O ---> R₂C=CHR'
Ph₃P=CHR', THF

Synthesis of Alkynes

Alkyne chain extension (section 6.10)

R-CCNa + Br-R' ---> R-CC-R'

Synthesis of Alcohols

From alkenes (sections 4.5, 4.7-4.9, 20.6)

R₂C=CR₂ ---> (OH)R₂C-CR₂X
R₂C=CR₂ ---> (OH)R₂C-CR₂H
R₂C=CR₂ ---> (OH)R₂C-CR₂H
R₂C=CR₂ ---> (OH)R₂C-CR₂H

R₂C=CR₂ ---> (OH)R₂C-CR₂(OH)

.
.
X₂ (X = Cl, Br) in water (halohydrin reaction)
1. BH₃, THF; 2. H₂O₂, OH^- (hydroboration) [anti-Mark.]
H+ (aq) [Markovnikov]
1. Hg(OAc)₂, H₂O, THF; 2. NaBH₄ [Markovnikov]
1. OsO₄; 2. NaHSO₃, H₂O

Cleavage of ethers (12.6)
R-O-R' ---> R-OH + R'-X

H-X in H₂O (X = Br, I)

Reduction of carbonyl (18.4, 20.1, 18.7)

R-C(=O)-R' ---> R-CH(OH)-R'

R-C(=O)-R' ---> R"RC(OH)-R'

R₂C=O ---> R₂C(OH)₂

R₂C=O ---> R₂(OH)C-CN

1. NaBH₄, ethanol; 2. H₃O⁺ (aldehyde or ketone)
H₂, Raney Ni (aldehyde or ketone)

1. R"-MgBr; 2. H₃O⁺ (Grignard reaction)

H⁺, H₂O
OH^-, H₂O

CN^-, HCl

From carboxyl (20.1)

R-C(=O)-O-R' ---> RCH₂OH + HO-R'
R-C(=O)-O-R' ---> R"₂RC-OH + HO-R
RC(=O)-O-R" ---> RHC=O + HO-R"

1. LiAlH₄; 2. H₃O⁺ (carboxylic acid or ester)
1. R"-MgBr; 2. H₃O⁺ (Grignard reaction, happens twice)

1. DIBAH, toluene; 2. H₃O⁺ (esters only)

Synthesis of Ethers

Alcohol plus halide (Williamson synthesis) (section 11.9)
R-OH ---> R-O-R'
1. NaH, THF; 2. R'-X

Alkoxymercuration - Markovnikov (section 4.8)
RHC=CR₂ ---> RH₂C-CR₂-O-R'
1. R'-OH, (CF₃CO₂)₂Hg; 2. NaBH₄

Halohydrin (section 4.5)
R₂C=CR₂ ---> (OR')R₂C-CR₂X
X₂ (X = Cl, Br) in alcohol (R'-OH)

Synthesis of acetal (section 18.8)
R₂C=O ---> R₂C(OR')₂

2 R'-OH, acid catalyst
[NOTE: can use a 1 diol instead of 2 alcohols]

Synthesis of Carbonyls

From alkene (section 20.8)
R₂C=CR'₂ ---> R₂C=O + O=CR'₂

1. O₃; 2. Zn / H₃O⁺ [stops at aldehyde]
KMnO₄, H₃O⁺, heat [continues to acid if aldehyde initially made]

From 1,2-diol (section 20.7)
(OH)R₂C-CR₂(OH) ---> R₂C=O + O=CR'₂
HIO₄ in H₂O

From alkyne (through enol form) (sections 6.6, 6.7, 20.9)

R-CC-R ---> R-CH₂-C(=O)-R (ketone)
R-CC-H ---> R-CH₂-C(=O)-H (aldehyde)
R-CC-H ---> R-C(=O)-CH₃ (ketone)
R-CC-R ---> R-C(=O)-C(=O)-R

1. BH₃, THF; 2. H₂O₂, OH^- (hydroboration) [no selectivity]
1. BR₃, THF; 2. H₂O₂, OH^- (hydroboration) [anti-Mark]
H₂SO₄ (H⁺), H₂O [Markovnokov]
KMnO₄, OH^-

Oxidation of alcohol (section 20.2)
[1^o alcohol gives aldehyde, 2^o gives ketone]
RR'HC-OH ---> RR'C=O

PCC in CH₂Cl₂
1. (CH₃)₂S=O, (ClCO)₂, -60^oC; 2. triethylamine [Swern]

secondary alcohol oxidation with Cr⁶⁺(section 20.2)
R₂HC-OH ---> R₂C=O

CrO₃ in acidic (H⁺) acetone
Na₂Cr₂O₇ in H₂SO₄

from ester (aldehyde created) (section 20.1)
RC(=O)-O-R" ---> RHC=O + HO-R"
1. DIBAH, toluene; 2. H₃O⁺ (esters only)

Synthesis of Carboxyls

Acid from alkyne (section 20.9)

R₁-CC-R₂ ---> R₁-COOH + HOOC-R₂

1. O₃, -78^o; 2. H₂O

From alkene (section 20.8)
R₂C=CHR' ---> R₂C=O + R'COOH
KMnO₄, H₃O⁺, heat

Acid from aldehyde (section 20.3)
R-C(=O)-H ---> R-COOH

CrO₃, H⁺
Na₂Cr₂O₇ in H₂SO₄
1. Ag₂O, NH₃; 2. H₃O⁺ [Tollen's reagent]

primary alcohol oxidation with Cr⁶⁺ (section 20.2)
RH₂C-OH ---> RCOOH

CrO₃ in acidic (H⁺) acetone
Na₂Cr₂O₇ in H₂SO₄

Reactions of Functional Groups

Reactions of Alkanes

Formation of alkyl halides (section 9.2)

C_nH_2n+2 ---> C_nH_(2n+2)-yX_y

X₂, hv (X = Cl, Br)

Reactions of Alkyl Halides

Reaction with deprotonated alkyne (sections 6.9-6.10) - see also, Grignard reactions
R-CC-H ---> R-CC:^-
R-CC:^- + R'-X ---> R-CC-R'

NaNH₂ (or another strong base)
substitution step (X = Br usually)

Formation of alkene (section 11.2)
R₂HC-CR₂X ---> R₂C=CR₂

OH^- (aq)
OH^- or CH₃CH₂O^- in ethanol
LDA in ether

Reactions of Alkenes

Hydrogenation (section 4.11)
R₂C=CR₂ ---> HR₂C-CR₂H
H₂, Pd / C

Addition of X₂ (section 4.7, Experiment 5)
R₂C=CR₂ ---> XR₂C-CR₂X
X₂ in CH₂Cl₂ (X = Cl, Br)

Addition of HX - Markovnikov (section 4.1)
HRC=CR₂ ---> H₂RC-CR₂X

HX in ether (X = Cl, Br)
KI in H₃PO₄ (X = I)

Allylic bromination (section 9.5)
R₂C=CR-CH₂-R ---> R₂C=CR-CHBr-R
NBS in CCl₄

Synthesis of alcohols (or ethers) (sections 4.5, 4.7-4.9, 20.6)

R₂C=CR₂ ---> (OR')R₂C-CR₂X
R₂C=CR₂ ---> (OH)R₂C-CR₂H
R₂C=CR₂ ---> (OH)R₂C-CR₂(OH)
RHC=CR2 ---> RH₂C-CR₂-O-R'
RHC=CR2 ---> RH₂C-CR₂-O-R'
X₂ (X = Cl, Br) in water (R' = H) or an alcohol (R' = alkyl)
1. BH₃, THF; 2. H₂O₂, OH^- (hydroboration) [anti-Mark.]
1. OsO₄; 2. NaHSO₃, H₂O
1. R'-OH, (CF₃CO₂)₂Hg; 2. NaBH₄ [Markovnikov]
H+ (aq) [Markovnikov]

Synthesis of carbonyl (section 20.8)
R₂C=CR'₂ ---> R₂C=O + O=CR'₂

1. O₃; 2. Zn / H₃O⁺
KMnO₄, H₃O⁺, heat [continues to acid if possible]

Reactions of Alkynes

Addition of X₂ (section 6.5)
RCCR ---> RX₂C-CX₂R
X₂ in CH₂Cl₂ (X = Cl, Br)

Addition of HX - Markovnikov (section 6.5)
RCCR ---> RH₂C-CX₂R
HX in ether (X = Cl, Br)

Hydrogenation (section 6.8)
RCCR ---> RH₂C-CH₂R
R-CC-R ---> RHC=CHR (cis)
R-CC-R ---> RHC=CHR (trans)
H₂, Pd / C
H₂, Lindlar catalyst
Li, NH₃

Deprotonation and reactions with alkyl halide (sections 6.9-6.10)
R-CC-H ---> R-CC-R'
1. NaNH₂; 2. R'-X

Reactions of Alcohols

Dehydration (section 12.5, Experiment 4)
R₂HC-CR₂OH ---> R₂C=CR₂

H⁺, (aq), heat (e.g., H₂SO₄, H₂O, THF, 50^oC)
H⁺, THF, 25^oC (3^o alcohols)
POCl₃, pyridine, 0^oC (2^o, 3^o alcohols)

Conversion to alkyl halide (sections 12.1, 12.3, Experiment 6)
R₃C-OH ---> R₃C-X

HX in ether (X = Cl, Br, I, usually 3^o alcohols)
SOCl₂ in pyridine (X = Cl, 1^o or 2^o alcohols)
PBr₃ in ether (X = Br, 1^o or 2^o alcohols)

Diol to carbonyl (section 20.7)
(OH)R₂C-CR₂(OH) ---> R₂C=O + O=CR'₂
HIO₄ in H₂O

Conversion to ether (Williamson synthesis) (section 11.9)

R-OH ---> R-O-R'

1. NaH, THF (deprotonation of alcohol to give R-O^-)
2. R'-X (substitution of X^- with R-O^-)

Oxidation of alcohol (section 20.2)
RR'HC-OH ---> RR'C=O

[primary alcohol gives aldehyde, secondary gives ketone]

PCC in CH₂Cl₂1. (CH₃)₂S=O, (ClCO)₂, -60^oC; 2. triethylamine [Swern]

secondary alcohol oxidation with Cr⁶⁺ (section 20.2)
R₂HC-OH ---> R₂C=O

CrO₃ in acidic (H⁺) acetone
Na₂Cr₂O₇ in H₂SO₄

primary alcohol oxidation with Cr⁶⁺ (section 20.2)
RH₂C-OH ---> RCOOH

CrO₃ in acidic (H⁺) acetone
Na₂Cr₂O₇ in H₂SO₄

Reactions of Carbonyls

Reduction of carbonyl (18.4, 20.1)

R-C(=O)-R' ---> R-CH(OH)-R'

R-C(=O)-R' ---> R"RC(OH)-R'

1. NaBH₄, ethanol; 2. H₃O⁺ (aldehyde or ketone)
H₂, Raney Ni (aldehyde or ketone)

1. R"-MgBr; 2. H₃O⁺ (Grignard reaction)

Acid from aldehyde (section 20.3)
R-C(=O)-H ---> R-COOH

CrO₃, H⁺
Na₂Cr₂O₇ in H₂SO₄
1. Ag₂O, NH₃; 2. H₃O⁺ [Tollen's reagent]

From carbonyls (section 18.6)
R-C(=O)-R' ---> C-CH₂-R'
(both aldehydes and ketones)
H₂NNH₂, OH^-, heat [Wolff-Kishner reaction]

Addition of H₂O or HCN (section 18.4, 18.7)
R₂C=O ---> R₂C(OH)₂

R₂C=O ---> R₂(OH)C-CN
H⁺, H₂O
OH^-, H₂O
CN^-, HCl

Synthesis of acetal (section 18.8)
R₂C=O ---> R₂C(OR')₂

2 R'-OH, acid catalyst
[NOTE: can use 1 diol instead of 2 alcohols]

Conversion to alkene (Wittig Reaction) (section 18.10)
R₂C=O ---> R₂C=CHR'
Ph₃P=CHR', THF

Reactions of Carboxyls

Reduction to alcohols (section 20.1)
RC(=O)-O-R" --->   R₂HC-OH + HO-R"
RC(=O)-O-R" --->   R'₂RC-OH + HO-R"
RC(=O)-O-R" --->   RHC=O + HO-R"
1. LiAlH₄, ether; 2. H₃O⁺ [carboxylic acid or ester]
1. R'MgBr, ether; 2. H₃O⁺ [esters, Grignard happens twice]
1. DIBAH, toluene; 2. H₃O⁺      (esters only)

Reactions of Ethers

Cleavage of ethers (section 12.6)
R-O-R' ---> R-OH + R'-X
H-X in H₂O (X = Br, I)

Last updated, November 18, 2005
Page maintained by Craig MacKinnon

From alkanes (Section 9.2) C_nH_2n+2 ---> C_nH_(2n+2)-yX_y	X₂, hv (X = Cl, Br) [NOTE: hv = light]
Addition of X₂ to alkenes and alkynes (sections 4.7, 6.5, Experiment 5) R₂C=CR₂ ---> XR₂C-CR₂X	X₂ in CH₂Cl₂ (X = Cl, Br)
Addition of HX to alkene and alkyne - Markovnikov (sections 4.1, 6.5) HRC=CR₂ ---> H₂RC-CR₂X	HX in ether (X = Cl, Br) KI in H₃PO₄ (X = I)
Addition of HX to alkene, anti-Markovnikov (section 4.10) HRC=CR₂ ---> HXRC-CR₂H	HBr with peroxide
Halohydrin reaction (section 4.7) R₂C=CR₂ ---> (OR')R₂C-CR₂X	X₂ (X = Cl, Br) in water (R' = H) or an alcohol (R' = alkyl)
Allylic bromination (section 9.5) R₂C=CR-CH₂-R ---> R₂C=CR-CHBr-R	NBS with peroxide
Conversion from alcohol (sections 12.1, 12.3, Experiment 6) R₃C-OH ---> R₃C-X	HX in ether (X = Cl, Br, I, usually 3^o alcohols) SOCl₂ in pyridine (X = Cl, 1^o or 2^o alcohols) PBr₃ in ether (X = Br, 1^o or 2^o alcohols)
Cleavage of ethers (section 12.6) R-O-R' ---> R-OH + R'-X	H-X in H₂O (X = Br, I)

Dehydration of alcohol (section 12.5, Experiment 4) R₂HC-CR₂OH ---> R₂C=CR₂	H⁺ (aq), heat (e.g., H₂SO₄, H₂O, THF, 50^oC) H⁺, THF, 25^oC (3^o alcohols) POCl₃, pyridine, 0^oC (2^o, 3^o alcohols)
From alkyl halide (E1 or E2 reaction) (section 11.2) R₂HC-CR₂X ---> R₂C=CR₂	OH^- (aq) or OH^- in ethanol CH₃CH₂O^- in ethanol LDA in ether
From alkyne (section 6.8) R-CC-R ---> RHC=CHR (cis) R-CC-R ---> RHC=CHR (trans)	H₂, Lindlar catalyst Li (or Na), NH₃
From carbonyl (Wittig Reaction) (section 18.10) R₂C=O ---> R₂C=CHR'	Ph₃P=CHR', THF

From alkenes (sections 4.5, 4.7-4.9, 20.6) R₂C=CR₂ ---> (OH)R₂C-CR₂X R₂C=CR₂ ---> (OH)R₂C-CR₂H R₂C=CR₂ ---> (OH)R₂C-CR₂H R₂C=CR₂ ---> (OH)R₂C-CR₂H R₂C=CR₂ ---> (OH)R₂C-CR₂(OH)	. . X₂ (X = Cl, Br) in water (halohydrin reaction) 1. BH₃, THF; 2. H₂O₂, OH^- (hydroboration) [anti-Mark.] H+ (aq) [Markovnikov] 1. Hg(OAc)₂, H₂O, THF; 2. NaBH₄ [Markovnikov] 1. OsO₄; 2. NaHSO₃, H₂O
Cleavage of ethers (12.6) R-O-R' ---> R-OH + R'-X	H-X in H₂O (X = Br, I)
Reduction of carbonyl (18.4, 20.1, 18.7) R-C(=O)-R' ---> R-CH(OH)-R' R-C(=O)-R' ---> R"RC(OH)-R' R₂C=O ---> R₂C(OH)₂ R₂C=O ---> R₂(OH)C-CN	1. NaBH₄, ethanol; 2. H₃O⁺ (aldehyde or ketone) H₂, Raney Ni (aldehyde or ketone) 1. R"-MgBr; 2. H₃O⁺ (Grignard reaction) H⁺, H₂O OH^-, H₂O CN^-, HCl
From carboxyl (20.1) R-C(=O)-O-R' ---> RCH₂OH + HO-R' R-C(=O)-O-R' ---> R"₂RC-OH + HO-R RC(=O)-O-R" ---> RHC=O + HO-R"	1. LiAlH₄; 2. H₃O⁺ (carboxylic acid or ester) 1. R"-MgBr; 2. H₃O⁺ (Grignard reaction, happens twice) 1. DIBAH, toluene; 2. H₃O⁺ (esters only)

Alcohol plus halide (Williamson synthesis) (section 11.9) R-OH ---> R-O-R'	1. NaH, THF; 2. R'-X
Alkoxymercuration - Markovnikov (section 4.8) RHC=CR₂ ---> RH₂C-CR₂-O-R'	1. R'-OH, (CF₃CO₂)₂Hg; 2. NaBH₄
Halohydrin (section 4.5) R₂C=CR₂ ---> (OR')R₂C-CR₂X	X₂ (X = Cl, Br) in alcohol (R'-OH)
Synthesis of acetal (section 18.8) R₂C=O ---> R₂C(OR')₂	2 R'-OH, acid catalyst [NOTE: can use a 1 diol instead of 2 alcohols]

From alkene (section 20.8) R₂C=CR'₂ ---> R₂C=O + O=CR'₂	1. O₃; 2. Zn / H₃O⁺ [stops at aldehyde] KMnO₄, H₃O⁺, heat [continues to acid if aldehyde initially made]
From 1,2-diol (section 20.7) (OH)R₂C-CR₂(OH) ---> R₂C=O + O=CR'₂	HIO₄ in H₂O
From alkyne (through enol form) (sections 6.6, 6.7, 20.9) R-CC-R ---> R-CH₂-C(=O)-R (ketone) R-CC-H ---> R-CH₂-C(=O)-H (aldehyde) R-CC-H ---> R-C(=O)-CH₃ (ketone) R-CC-R ---> R-C(=O)-C(=O)-R	1. BH₃, THF; 2. H₂O₂, OH^- (hydroboration) [no selectivity] 1. BR₃, THF; 2. H₂O₂, OH^- (hydroboration) [anti-Mark] H₂SO₄ (H⁺), H₂O [Markovnokov] KMnO₄, OH^-
Oxidation of alcohol (section 20.2) [1^o alcohol gives aldehyde, 2^o gives ketone] RR'HC-OH ---> RR'C=O	PCC in CH₂Cl₂ 1. (CH₃)₂S=O, (ClCO)₂, -60^oC; 2. triethylamine [Swern]
secondary alcohol oxidation with Cr⁶⁺(section 20.2) R₂HC-OH ---> R₂C=O	CrO₃ in acidic (H⁺) acetone Na₂Cr₂O₇ in H₂SO₄
from ester (aldehyde created) (section 20.1) RC(=O)-O-R" ---> RHC=O + HO-R"	1. DIBAH, toluene; 2. H₃O⁺ (esters only)

Acid from alkyne (section 20.9) R₁-CC-R₂ ---> R₁-COOH + HOOC-R₂	1. O₃, -78^o; 2. H₂O
From alkene (section 20.8) R₂C=CHR' ---> R₂C=O + R'COOH	KMnO₄, H₃O⁺, heat
Acid from aldehyde (section 20.3) R-C(=O)-H ---> R-COOH	CrO₃, H⁺ Na₂Cr₂O₇ in H₂SO₄ 1. Ag₂O, NH₃; 2. H₃O⁺ [Tollen's reagent]
primary alcohol oxidation with Cr⁶⁺ (section 20.2) RH₂C-OH ---> RCOOH	CrO₃ in acidic (H⁺) acetone Na₂Cr₂O₇ in H₂SO₄

Reaction with deprotonated alkyne (sections 6.9-6.10) - see also, Grignard reactions R-CC-H ---> R-CC:^- R-CC:^- + R'-X ---> R-CC-R'	NaNH₂ (or another strong base) substitution step (X = Br usually)
Formation of alkene (section 11.2) R₂HC-CR₂X ---> R₂C=CR₂	OH^- (aq) OH^- or CH₃CH₂O^- in ethanol LDA in ether

Hydrogenation (section 4.11) R₂C=CR₂ ---> HR₂C-CR₂H	H₂, Pd / C
Addition of X₂ (section 4.7, Experiment 5) R₂C=CR₂ ---> XR₂C-CR₂X	X₂ in CH₂Cl₂ (X = Cl, Br)
Addition of HX - Markovnikov (section 4.1) HRC=CR₂ ---> H₂RC-CR₂X	HX in ether (X = Cl, Br) KI in H₃PO₄ (X = I)
Allylic bromination (section 9.5) R₂C=CR-CH₂-R ---> R₂C=CR-CHBr-R	NBS in CCl₄
Synthesis of alcohols (or ethers) (sections 4.5, 4.7-4.9, 20.6) R₂C=CR₂ ---> (OR')R₂C-CR₂X R₂C=CR₂ ---> (OH)R₂C-CR₂H R₂C=CR₂ ---> (OH)R₂C-CR₂(OH) RHC=CR2 ---> RH₂C-CR₂-O-R' RHC=CR2 ---> RH₂C-CR₂-O-R'	X₂ (X = Cl, Br) in water (R' = H) or an alcohol (R' = alkyl) 1. BH₃, THF; 2. H₂O₂, OH^- (hydroboration) [anti-Mark.] 1. OsO₄; 2. NaHSO₃, H₂O 1. R'-OH, (CF₃CO₂)₂Hg; 2. NaBH₄ [Markovnikov] H+ (aq) [Markovnikov]
Synthesis of carbonyl (section 20.8) R₂C=CR'₂ ---> R₂C=O + O=CR'₂	1. O₃; 2. Zn / H₃O⁺ KMnO₄, H₃O⁺, heat [continues to acid if possible]

Addition of X₂ (section 6.5) RCCR ---> RX₂C-CX₂R	X₂ in CH₂Cl₂ (X = Cl, Br)
Addition of HX - Markovnikov (section 6.5) RCCR ---> RH₂C-CX₂R	HX in ether (X = Cl, Br)
Hydrogenation (section 6.8) RCCR ---> RH₂C-CH₂R R-CC-R ---> RHC=CHR (cis) R-CC-R ---> RHC=CHR (trans)	H₂, Pd / C H₂, Lindlar catalyst Li, NH₃
Deprotonation and reactions with alkyl halide (sections 6.9-6.10) R-CC-H ---> R-CC-R'	1. NaNH₂; 2. R'-X

Dehydration (section 12.5, Experiment 4) R₂HC-CR₂OH ---> R₂C=CR₂	H⁺, (aq), heat (e.g., H₂SO₄, H₂O, THF, 50^oC) H⁺, THF, 25^oC (3^o alcohols) POCl₃, pyridine, 0^oC (2^o, 3^o alcohols)
Conversion to alkyl halide (sections 12.1, 12.3, Experiment 6) R₃C-OH ---> R₃C-X	HX in ether (X = Cl, Br, I, usually 3^o alcohols) SOCl₂ in pyridine (X = Cl, 1^o or 2^o alcohols) PBr₃ in ether (X = Br, 1^o or 2^o alcohols)
Diol to carbonyl (section 20.7) (OH)R₂C-CR₂(OH) ---> R₂C=O + O=CR'₂	HIO₄ in H₂O
Conversion to ether (Williamson synthesis) (section 11.9) R-OH ---> R-O-R'	1. NaH, THF (deprotonation of alcohol to give R-O^-) 2. R'-X (substitution of X^- with R-O^-)
Oxidation of alcohol (section 20.2) RR'HC-OH ---> RR'C=O [primary alcohol gives aldehyde, secondary gives ketone]	PCC in CH₂Cl₂1. (CH₃)₂S=O, (ClCO)₂, -60^oC; 2. triethylamine [Swern]
secondary alcohol oxidation with Cr⁶⁺ (section 20.2) R₂HC-OH ---> R₂C=O	CrO₃ in acidic (H⁺) acetone Na₂Cr₂O₇ in H₂SO₄
primary alcohol oxidation with Cr⁶⁺ (section 20.2) RH₂C-OH ---> RCOOH	CrO₃ in acidic (H⁺) acetone Na₂Cr₂O₇ in H₂SO₄

Reduction of carbonyl (18.4, 20.1) R-C(=O)-R' ---> R-CH(OH)-R' R-C(=O)-R' ---> R"RC(OH)-R'	1. NaBH₄, ethanol; 2. H₃O⁺ (aldehyde or ketone) H₂, Raney Ni (aldehyde or ketone) 1. R"-MgBr; 2. H₃O⁺ (Grignard reaction)
Acid from aldehyde (section 20.3) R-C(=O)-H ---> R-COOH	CrO₃, H⁺ Na₂Cr₂O₇ in H₂SO₄ 1. Ag₂O, NH₃; 2. H₃O⁺ [Tollen's reagent]
From carbonyls (section 18.6) R-C(=O)-R' ---> C-CH₂-R' (both aldehydes and ketones)	H₂NNH₂, OH^-, heat [Wolff-Kishner reaction]
Addition of H₂O or HCN (section 18.4, 18.7) R₂C=O ---> R₂C(OH)₂ R₂C=O ---> R₂(OH)C-CN	H⁺, H₂O OH^-, H₂O CN^-, HCl
Synthesis of acetal (section 18.8) R₂C=O ---> R₂C(OR')₂	2 R'-OH, acid catalyst [NOTE: can use 1 diol instead of 2 alcohols]
Conversion to alkene (Wittig Reaction) (section 18.10) R₂C=O ---> R₂C=CHR'	Ph₃P=CHR', THF