Organic Chemistry

Draw This Structure

100

Adamantane 

200

Furan

300

2,7-dibromobicyclo[2.2.1]heptane 

400

The Tosylate of Benzyl Alcohol 

500

Organoborane formed from reaction of 1-butyne with sia2BH

Nomenclature

100

provide the name:

200

provide the name:

300

provide the name:

400

provide the name:

500

provide the name:

pKa’s

100

What is the pKa of ammonia? Write ammonia out.

PKa= 38 NH₃

200

What is the pKa of acetone? Write acetone out.

PKa = ~20 (CH₃)₂CO

300

What is a base strong enough to deprotonate ethanol?

Any base with conjugate acid of > or = 18

Na⁺ N^-H₂ 

400

Which is the stronger acid?

H₃C-OH or H₃C-SH

H₃C-SH

500

Rank in order of decreasing pKa’s and write each Lewis structure.

Ethanol, ammonium, alkanes, Acetic Acid, alkynes, Water, Hydrochloric acid, Alkene, ammonia, Hydronium 

Alkane 51 > alkene 44 > Ammonia 38 > alkyne 25 > ethanol 16 > water 15.7 > ammonium 9.2 > Acetic acid 4.8 > Hydronium -1.7 > Hydrochloric acid -7.0

Reactions

100

Cyclohexene reaction with H-Br 

200

1-methylcyclohexene reacting with 1.) BH3 2.)H2O2,NaOH

300

Radical reaction of 2-methylbutane reacting with Br2, hv

400

Reaction of 1,2-dimethylcyclohexene with H2, Pd or Pt

500

The E1 reaction of 2-methylpentan-3-ol with H2SO4

SN1/SN2

100

A carbocation intermediate forms 

SN1

200

The rate of reaction doubles when nucleophile conc doubles 

SN2

300

A vinyl Halide does not undergo this reaction

Both SN1 and SN2

400

sketch a potential energy diagram for an exothermic SN2 reaction of NaCN with (S)-2-iodobutane

500

provide 3D drawing of the transition state structure for the exothermic SN2 Rxn of NaCN with (S)-2-iodobutane