CHEM 2261 Test 3 Reactions (Ch. 7, 8, 10, 13) Nauman Questions with Solved Solutions.

CHEM 2261 Test 3 Reactions (Ch. 7, 8,
10, 13) Nauman Questions with Solved
Solutions.
2 consecutive eliminations

Products: 2 C=C or 1 Carbon Carbon triple bond

Reagents: NaNH2, THF/DMF, heat - Answer Synthesis of Alkynes via consecutive elimination



Form alkane from alkene

syn addition

Reagents: H2, Pd/Pt/Ni - Answer Addition of H2 to alkenes--hydrogenation



1. Alkyne to alkane

Reagents: Excess/ H2, Pd/C

2. Lindlar's Catalyst (cis-alkene)

Reagents: H2, Lindlar's Catalyst

3. Na or Li, NH3 (liq), -78 degrees C (trans-alkene)

Reagents: Na or Li, NH3 (liq), -78 degrees C - Answer Addition of H2 to alkynes

**Do NOT have to know mechanism**



Multistep Synthesis

Reagents: NANH2, 2 degree, 1 degree or methyl halides

Sn2 Reaction - Answer Alkyne Synthesis



Carbocation intermediate

Carbocation rearrangement

Markovnikov

Reagents: HCl, HBr, HI

H--> attaches to C with greatest number of H's

X--> attaches to C with least number of H's - Answer Addition of hydrogen halides (HX)

**Know Mechanism**



Carbocation intermediate

Carbocation rearrangement (hydride or methyl shift)

, Markovnikov

Reagents: H3O+, H2O/ H+, [H2SO4]

most substituted alcohol produced - Answer Addition of water (H2O+/ H+) and alcohols
(ROH/ H+)

**Know Mechanism**



Bromonium intermediate

anti-addition

cis/ trans symmetrical

Reagents: Cl2/ CH2Cl2 or Br2/ CH2Cl2)

Halohydrin-->molecules with OH group and halide

Reagents: Cl2 or Br2/ H2O

OH goes on more substituted Carbon

Markovnikov

No Carbocation rearrangement

Anti-addition

bromonium intermediate - Answer Addition of Halogens (Cl2/ CH2Cl2 or Br2/ CH2Cl2)



Markovnikov

Mercuronium intermediate

2 Steps

1. Oxymercuration--> Reagent: Hg(OAc)2

2. Demercuration--> Reagent: NaBH4 - Answer Oxymercuration-Demercuration



Anti-Markovnikov--> H goes to C with least number of H's

syn-addition

Forms 2 products when cyclic

Reagents: BH3, THF/ H2O2, OH-, H2O - Answer Hydroboration-Oxidation



Anti-Markovnikov

Free radical addition

3 steps

1. Initiation

2. Propagation

3. Termination