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OChem II Midterm One Review
Second semester organic chemistry review for midterm one chapters 9, 12-15
31
Organic Chemistry
Undergraduate 3
02/15/2016

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Cards

Term
Alkene or alkyne under NaNH2/NM3
Definition
Removes H on the terminal end of the conjugated carbon, leaves lone pair and - on that carbon
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Alkene or alkyne under H2 and lindlar's catalyst (Pd/C)
Definition

Alkene gives alkane

Alkyne gives alkene

Term
Alkene under Br2, Hv
Definition
One Br on each of the two carbons involved in the double bond
Term
Common solvents for proton NMR
Definition

Really anything with D instead of H (CDCl3, CD3CN, D2O) and CCl4

If it has an H it's not a common solvent 

Term
Location of a signal on a proton NMR says...
Definition
The electronic environment of absorbing protons
Term
If the MHz of the spectrometer used changes, does the location of the signal?
Definition

NO

i.e. if a signal is at 3.5ppm with a 60-MHz spec, it's at 3.5ppm with a 300-MHz spec

Term
What is the base peak of a mass spec?
Definition

The tallest peak and the most abundant ion

Not always M•+

Term
Separation of ions in mass spec is done by...
Definition
Mass to charge ratio
Term
How to find m/z values for a given compound
Definition

m/z value is generalized molecular weight of compound

C=12

O=16

H=1

Term

Reactions with LAH/water

Aldehyde -> 

Carboxylic acid -> 

Ester ->

Ketone ->

Definition

Aldehyde -> primary alc

Carboxylic acid -> primary alc

Ester -> primary alc

Ketone -> secondary alc

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Definition
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Term

Give products 

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Definition
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Term

Give products

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Definition
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Term
How to determine oxidation levels
Definition

1. find molecular formula

2. C=X, H=1, O=-2

3. set equation = 0 and solve for X

4. greatest X > lowest X for oxidation level 

Term

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Definition
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Definition
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Term
Reduction reactions...
Definition

Gain a proton H+

X to H

double bond to single bond

carbonyl to alcohol

Term
What can NaBH4 reduce?
Definition

aldehyde to primary alc

ketone to secondary alc

won't reduce carb. acid or ester

Term
Ketone under H2/Pd
Definition
removes carbonyl group (=O) but doesn't change the remainder of the compound
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