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OC 2 Lab Midterm

front 1

Chlorination of Heptane

What was the purpose of the lab? (2)

back 1

  1. Demonstrate the formation of chloroheptane via the radical chlorination of heptane
  2. To determine the relative reactivities primary vs secondary Hs

front 2

Chlorination of Heptane

What is the mechanism?

back 2

front 3

Chlorination of Heptane

Why is it important to not expose sulfuryl chloride to H2O & acetone.

And why should we keep it in the hood?

back 3

  1. Sulfuryl chloride reacts vigorously w/ H2O & acetone → sulfuryl chloride gets consumed ∴ yield decreases.
  2. Sulfuryl chloride is kept in the hoood as it's toxic/harmful if inhaled.

front 4

Chlorination of Heptane

What chemical rxn is occuring in the gas trap?

Write out the chemical rxn

back 4

  1. Neutralization rxn
  2. NaOH + HCl → NaCl + H2O

front 5

Chlorination of Heptane

Calculate the relative reactivity of the Cl radical for 1o, 2o, , and 3o Hs

back 5

front 6

Chlorination of Heptane

Why is the 2o chloroheptane have a greater reactivity than the 1o? (3)

back 6

  1. 2o more Hs (10) vs 1o Hs (6)
  2. 2o radical is more stable than the 1o radical
  3. 2o C-H bond is weaker (via inductive effect) ∴ easier to extract/break

front 7

Chlorination of Heptane

How is the GC supposed to be labeled?

back 7

front 8

Chlorination of Heptane

Perform the following calculations for this lab.

  1. AY
  2. TY
  3. PY
  4. Relative Reactivity

Important info:

  • 10 mL heptane
    • Density = .6975 g/mL
    • MM = 100.21 g
  • 15 mL sulfuryl chloride (SO2Cl2)
    • Density = 1.665 g/mL
    • MM = 134.98 g
  • Mass vial = 13.13 g
  • Mass vial + chloroheptane = 14.23 g
  • GC provided

back 8

front 9

Diels Alder

What is the purpose? (2)

back 9

  1. Demonstrate the Diels Alder reaction of E,E-2,4-hexadien-1-ol and maleic anhydride
  2. Verify the formation of Diels Alder (DA) product via 1H NMR and melting point

front 10

Diels Alder

What was the purpose of weighing the diene 1st?

back 10

it's sticky

front 11

Diels Alder

What is the purpose of using toluene for the rxn?

back 11

To allow for recrystallization. D/t toluene being nonpolar, when the solution is cooled (solubility ↓), the polar product will precipitate out & the impurities stay ∴ allowing for purification.

front 12

Diels Alder

Show how maleic anhydride is electrophilic.

back 12

front 13

Diels Alder

Assign the major IR stretches for the following compound.

back 13

front 14

Diels Alder

Complete the 1H NMR

back 14

front 15

Diels Alder

Complete the IR

back 15

front 16

Diels Alder

Perform the following calculations for this lab.

  1. AY
  2. TY
  3. PY

Important info:

  • .4038 g maleic anhydride
    • MM = 98.06 g/mol
  • .4023 g

back 16

front 17

Diels Alder

What was the literature mp?

back 17

156-159 ℃

front 18

Electrophilic Bromination

What is the purpose? (2)

back 18

  1. Demonstrate the Electrophilic Bromination reaction of acetanilide and potassium bromate
  2. Verify formation of N-(4-bromophenyl)acetamide (EB product) via 1H NMR

front 19

Electrophilic Bromination

Provide mechanism

back 19

front 20

Electrophilic Bromination

Using resonance, show how the amide group activates the ring & directs substitution at the ortho & para positions.

back 20

front 21

Electrophilic Bromination

What is the purpose of doing this rxn at room temp?

back 21

adding heat will cause BR to form too quickly & polybrominate

front 22

Electrophilic Bromination

Identify the peaks & determine the final structure for the following rxn.

back 22

front 23

Electrophilic Bromination

Perform the following calculations for this lab.

  1. AY
  2. TY
  3. PY

Important info:

  • .2064 g acetanilide
    • MM = 135.16 g/mol
  • .0852 g potassium bromate
    • MM = 167.0 g/mol
  • Mass watch glass = 20.563 g
  • Mass watch glass + DA product = 20.694 g

back 23

not supposed to use postassium bromate when calculating TY & PY

front 24

Electrophilic Bromination

Complete 1H NMR

back 24

front 25

Electrophilic Bromination

Complete Mass Spec

back 25

front 26

Friedel Crafts Alkylation

What is the purpose of the lab?

back 26

  1. Demonstrate the Friedel-Crafts Alkylation reaction of p-xylene and n-bromopropane
  2. Verify the formation of n-propyl and iso-propyl (FC Products) via Gas Chromatogram data

front 27

Friedel Crafts Alkylation

Provide mechanism

back 27

front 28

Friedel Crafts Alkylation

Why do we use aluminum chloride (AlCl3) in this rxn?

back 28

AlCl3 acts as a catalyst & by binding to the E+ to form a complex, it increases the electrophilicity of the E+

front 29

Friedel Crafts Alkylation

What happens if the AlCl3 gets wet?

back 29

AlCl3 is very hydroscopic → gets consumed by absorbing H2O from the atmosphere ∴ affects PY

front 30

Friedel Crafts Alkylation

Why do we use a drying tube w/ calcium chloride (CaCl2)?

back 30

drying agent → absorbs H2O ∴ prevents H2O from messing up the PY

front 31

Friedel Crafts Alkylation

Why did we use a saturated NaCl solution for the extraction?

back 31

will force ions from the organic layer into the aqueous layer → clear organic & aqueous layers formed ∴ better extraction

front 32

Friedel Crafts Alkylation

Provide the mechanism, product, & labeled NMR based on the following.

back 32

front 33

Friedel Crafts Alkylation

Perform the following calculations for this lab.

  1. AY
  2. TY
  3. PY

Important info:

  • 2 mL p-xylene
    • Density = .861 g/mL
    • MM = 106.17 g/mol
  • .8 mL n-bromopropane
    • Density = 1.354 g/mL
    • MM = 122.99 g/mol
  • Mass watch glass = 21.30 g
  • Mass watch glass + product = 22.03 g

back 33

front 34

Friedel Crafts Alkylation

What does the labeled GC look like?

back 34