Organic Chemistry 2 Jeopardy

NMR Spectroscopy

100

A method for determining the structure of a molecule through peaks corresponding to protons in the molecule

What is proton NMR spectroscopy

200

Chemical shift in NMR frequency is caused by this phenomenon where electron density is lesser and/or the presence of pi bonds in close proximity to protons

deshielding

300

Atoms that don't participate in NMR splitting

Chemically equivalent protons, protons attached to oxygens or nitrogens

400

Methyl group proton peaks and other saturated chain proton peaks can be found in this region on the NMR spectra 

1.5-0.0 ppm; upfield

500

Functional group that can be found in the 12.0-9.0 ppm region on NMR spectra

Protons in close proximity to carbonyl groups can be found here

Degree of Unsaturation

100

C₉H₈O₄

6

200

benzene ring

4

300

C₂₉H₅₀O₂

5

400

C₉H₁₃N

4

500

C₈H₁₁NO₃

3

Synthetic Transformation Reagents

100

Reagent that allows for anti-Markovnikov addition of H and Br

HBr and peroxides in the presence of heat or light

200

Reagent that allows for the cleavage of a C=C double bond and what is that process called

1: O₃

2: Zn and acetic acid

Called ozonolysis

300

Reagent(s) that allow for markovnikov addition of H and a halogen to an alkyne to end up with an alkane

Two portions of HX under cold, dark conditions (no peroxides) 

X=Br,Cl,F

400

Reagent that allows for radical bromonation of an alkane via SN2 

Br₂ and light or NBS and light

500

Reagent that allows for an S_N2 reaction to occur where an alkyne is lengthened via the addition of alkane 

1: NaNH₂ and a strong base 

2: an alkane with a good leaving group such as Cl, Br, I, or OTs

Radical Reactions

100

The trend of increasing radical halogenation reaction time as you go up the period table

I₂,Br_2,Cl₂,F₂

200

Bromine will preferentially attach to this kind of carbon

tertiary carbons

300

What kind of bonds do radical initiators prefer

C-H bonds

400

How radicals are created 

Br₂ is bombarded with intense light to yield a small number of radicals

500

The steps of a radical reaction

Initiation: radical species is created by being bombarded with intense light

Propagation: radical initiator cleaves an H from a C-H bond. A lone electron is left on that C and a H-X bond is created

Termination: The carbon with the single electron then takes another halogen radical species to form an R-X bond

IR Spectroscopy

100

Alcohol groups (O-H) can be visible at this frequency and looks like this:

3200-3650 cm^-1 as a broad and strong peak

200

A visual method for determining the possible functional groups in a molecule given the degree of unsaturation and the molecular formula

IR spectroscopy

300

The 1450-500 cm^-1 range in the IR can be used to help double check if a certain functional group peak farther down the spectra corresponds with a weaker peak in this region. This region is almost unique to any given molecule and can be difficult to read and is called 

The fingerprint region

400

Each type of bond when hit with IR light will absorb this light at different frequencies, hence allowing us to see certain functional groups via visible spectra peaks. By using reference tables of known absorption frequencies for varying functional groups, it is possible to determine the possible structure of a molecule given the molecular formula. 

How IR is possible

500

This functional group is visible between 1690-1680 as a strong peak

carbonyl group (C=O)