UW Chem 238 Final Exam Questions with 100% Correct Answers

UW Chem 238 Final Exam Questions with
100% Correct Answers
Alcohol to alkene

1. TsCl

2. Base

Alcohol to alkene (another way)

H2SO4 (H+)

(or H3PO4, or other strong acids)

Alcohol to alcohol (inverted)

1. TsCl

2. NaOH

Alcohol to ether

1. TsCl

2. NaOR

Alcohol to ether (another way)

1. Na(H)

2. RBr (R-X)

1° Alcohol to carboxylic acid

H2CrO4 (or K2Cr2O7)

1° Alcohol to aldehyde

PCC

,2° Alcohol to ketone

H2CrO4 or PCC

1° or 2° Alcohol to 1° or 2° R-Cl

SOCl2

1° to 2° Alcohol to 1° or 2° R-Br

Ph3PBr2

Alcohol to alkoxide

NaH + R-OH

Alcohol to alkoxide (another way)

2RO-H + 2Na

(1°, 2°, or 3°) Alcohol to (1°, 2°, or 3°) R-X

H-X (and protic solvent)

Alcohol to R-Nuc

1. TsCl

2. Nu:- (i.e. Br-, I-, Cl-, CN-, N3-)

Thiol to disulfide

[O] (air or I2)

Thiol to sulfonic acid (R-SO3H)

HNO3 or KMnO4 (strong oxidants)

Ether to alcohol (and R-X)

, H-X (I > Br > Cl, increasing reactivity as acid gets stronger)

Epoxide to alkyl chain with -OH and Nu (OH-R-O-Nu) showing SN2 mechanism

Nu:- (i.e. OH-, RO-, organolithium reagents) and (related (?)) protic solvent (EtOH, H2O) ??

Epoxide to alkyl chain with -OH and Nu (OH-R-O-Nu) showing SN1 mechanism

Nu:- (i.e. OH-, RO-, organolithium reagents) and H+ (acid) ??

Alkene to epoxide

mCPBA

Halohydrine w/ X and OH dihedral 180° from each other to epoxide

NaOH

Achiral alkene to chiral epoxide (enantiomer)

Ligand (chiral catalyst), Ti(OiPr4), and tBuO-O-H)

Alkoxide to ether (Williamson Ether Synthesis)

1° or 2° Alkyl Halide

Alkene to ether

1. Hg(OAC)2

2. Alkyl alcohol (R-OH)

3. NaBH4

1°, 2°, or 3° alcohol to ether (and water byproduct)

H+ (and another R-OH)

Alkene to ether