Organic Chemistry Test 1

Carbon wants to make __ bonds?

Carbon wants to make __ bonds?

4

Formal charge

Valence-sticks-dots

formal charge: oxygen with 1 single bond

-1

Formal charge: nitrogen with 4 bonds

+1

Octet rule exemptions

Be, B and anything n=3 or below can have more than an octet

Resonance vs Isomers

• Isomers have atoms in different places

• Resonance has charges in different places-electrons move around

Chain length: 1,2,3,4,5,6,7,8,9,10,11,12,20,30

Meth,eth,prop,but,pent,hex,hept,oct,non,dec,undec,Dedec,icosane,triacontane

Hybridization shortcut

Write, spppddddd and the number of electron groups

Single bonded carbons, double bonded carbons, triple bonded carbons hybridization

Sp3, sp2, sp

Bonds are strong when the length ain’t long

S-character shows how strong a bond is based on hybridization, sp is the strongest followed by sp2, sp3 and so on

Most electronegative elements

Can Not Clean Out Fridge, carbon nitrogen chlorine oxygen fluorine (in that order)

Acid strength pKas H-cl

-7

PKa Ch3CO2-H

Carboxylic acid, 4.8

PKa HO-H

15.7

CH3CH2O-H

16

PKas HC-triple bond-CH

25

Pkas H-H

35

PKas H2N-H

38

PKas CH2-double bond-CH2

44

PKas CH3-H

50

Low PKa=

=stronger acid

4 factors affect the acidity of HA

• element effects

• Inductive effects

• Resonance effects

• Hybridization effects

Common Lewis acids

BF3 and AlCl3

Lewis acids are called ___ and Lewis bases are called __

Electrophiles, nucleophiles

Alkane

Sigma bond

Alkene

Sigma + pi

Alkyne

Sigma + 2pi

Ex. CH3-Br

Alkyl Halide, r group with an x where x= a halogen (F,cl ,br,I)

ex. CH3-OH

Alcohol

Ex. CH3-O-CH3

Ether ( looks like a pregnant lady don’t it?)

Ex. CH3-NH2

Amine! My beloved <3. Basically if you see a nitrogen and only single bonds

Ex. CH3-S-H

Thiol, basically if you see a sulfur and its bonded to a hydrogen

Ex. CH3-S-CH3

Sulfide, sulfur bonded to r groups ( and not a direct hydrogen)

Ex. CH3CHO

Aldehyde, kinda like a ketone but with a hydrogen or a carboxylic acid but without oxygen

Ex. (CH3)2CO

Ketone, looks like a key!

Ex. CH3CO2H

Carboxylic acid, like a ketone with an additional alcohol group (OH)

Ex. CH3CO2CH3

Ester

Ex. CH3CONH2

Amide, it’s like an amine but with a ketone (fun fact: amides can result from a reaction between an amine and a carboxylic acid, that’s why they’re a mix!)

Ex. CH3COCl

Acid chloride