Organic Chemistry I: Exam 1

IUPAC prefix: meth-

1 carbon in main (longest) chain

IUPAC prefix: eth-

2 carbons in main (longest) chain

IUPAC prefix: prop-

3 carbons in main (longest) chain

IUPAC prefix: but-

4 carbons in main (longest) chain

IUPAC prefix: pent-

5 carbons in main (longest) chain

IUPAC prefix: hex-

6 carbons in main (longest) chain

IUPAC prefix: hept-

7 carbons in main (longest) chain

IUPAC prefix: oct-

8 carbons in main (longest) chain

IUPAC prefix: non-

9 carbons in main (longest) chain

IUPAC prefix: dec-

10 carbons in main (longest) chain

IUPAC prefix: undec-

11 carbons in main (longest) chain

IUPAC prefix: dodec-

12 carbons in main (longest) chain

IUPAC prefix: tridec-

13 carbons in main (longest) chain

IUPAC prefix: tetradec-

14 carbons in main (longest) chain

IUPAC prefix: pentadec-

15 carbons in main (longest) chain

IUPAC prefix: hexadec-

16 carbons in main (longest) chain

IUPAC prefix: heptadec-

17 carbons in main (longest) chain

IUPAC prefix: octadec-

18 carbons in main (longest) chain

IUPAC prefix: nonadec-

19 carbons in main (longest) chain

IUPAC prefix: eicos-

20 carbons in main (longest) chain

IUPAC saturation: -an-

only single bonds b/w carbons

IUPAC saturation: -en-

at least one double bond b/w carbons

IUPAC saturation: -yn-

at least one triple bond b/w carbons

class: alkanes

• general formula: RH

• common name: ethane

• common prefix/suffix: -ane

class: alkenes

• general formula: RR’C = CR”R”’

• common name: ethylene (ethene)

• common prefix/suffix: -ene

class: alkynes

• general formula: RC ≡ CR’

• common name: acetylene (ethyne)

• common prefix/suffix: -yne

class: arenes

• general formula: ArH^a

• common name: benzene

• common prefix/suffix: -ene

class: alkyl halides

• general formula: RX

• common name: ethyl chloride (chloroethane)

• common prefix/suffix: halide (halo-)

class: aryl halides

• general formula: ArX^a

• common name: chlorobenzene

• common prefix/suffix: halo-

class: alcohols

• general formula: ROH^a

• common name: ethyl alcohol (ethanol)

• common prefix/suffix: -ol

class: phenols

• general formula: ArOH^b

• common name: phenol

• common prefix/suffix: -ol

class: ethers

• general formula: ROR’

• common name: diethyl ether

• common prefix/suffix: ether

class: aldehydes

• general formula: RCHO

• common name: acetaldehyde (ethanal)

• common prefix/suffix: -aldehyde (al)

class: ketones

• general formula: RR’C = O

• common name: acetone (2-propane)

• common prefix/suffix: -one

class: carboxylic acids

• general formula: RCO₂H

• common name: acetic acid (ethanoic acid)

• common prefix/suffix: -ic acid (-oic acid)

class: acyl halides

• general formula: RCO₂Cl

• common name: ethanoyl chloride

• common prefix/suffix: -oyl halide

class: anhydrides

• general formula: RCOOCOR

• common name: ethanoic anhydride (acetic anhydride)

• common prefix/suffix: -oic anhydride

class: esters

• general formula: RCO₂R’

• common name: methyl acetate (methyl ethanoate)

• common prefix/suffix: -ate (-oate)

class: amides

• general formula: RCONHR’

• common name: N-methylacetamide

• common prefix/suffix: -amide

class: amines

• general formula: RNH₂, RNHR’, RNR’R”

• common name: -ethylamine

• common prefix/suffix: -amine

class: nitriles

• general formula: RC ≡ N

• common name: acetonitrile

• common prefix/suffix: -nitrile

class: nitro compounds

• general formula: ArNO_2'“

• common name: nitrobenzene

• common prefix/suffix: nitro-

class: thiols

• general formula: RSH

• common name: methaethiol

• common prefix/suffix: -thiol

class: sulfides

• general formula: RSR

• common name: dimethyl sulfide

• common prefix/suffix: -sulfide

in stable neutral organic molecules, H has…

one bond

in stable neutral organic molecules, C has…

four bonds + no lone pairs

in stable neutral organic molecules, N has…

three bonds + one lone pair

in stable neutral organic molecules, O has…

two bonds + two lone pairs

in stable neutral organic molecules, F, Cl, Br, and I have…

one bond + three lone pairs

which elements can contain 6 electrons in their valence shell?

boron and alumnium (group IIIA)

which elements can contain up to 10 electrons in their valence shell?

phosphorus

which elements can contain up to 12 electrons in their valence shell?

sulfur

formal charge equation

FC = neutral, unbonded valence electrons - (nonbonding electrons + ½ bonding electrons) [FC = VE - (NBE + 1/2BE)]

single bond

1 σ (sigma) bond

double bond

1 σ (sigma) bond + 1 π (pi) bond

triple bond

1 σ (sigma) bond + 2 π (pi) bond

sp hybridization

one triple bond or two double bonds (2σ + 2π)

sp2 hybridization

one double bond (3σ + π)

sp3 hybridization

single bonds (4σ)

infix: -an-

all single bonds

infix: -en-

one or more double bonds

infix: -yn-

one or more triple bonds

suffix: -e

compound class: hydrocarbon

suffix: -ol

compound class: alcohol

suffix: -al

compound class: aldehyde

suffix: -one

compound class: ketone

suffix: -oic acid

compound class: carboxylic acid

curved arrow

symbol used to show redistribution of valence electrons

• represents 2 electrons and indicates direction of movement

bronsted-lowry acid

proton donator

bronsted-lowry base

proton acceptor

strong acids have…

• high Ka

• low pKa

• greater electronegativity

• greater delocalization of negative charge in the conjugate base

• more electron withdrawing

lewis acid

electron acceptor

lewis base

electron donator

electrophiles

reagents that seek electrons to achieve a stable shell of electrons (octet rule)

• all lewis acids

nucleophiles

reagents that seek a positive center, like a positively-charged carbon atom

• all lewis bases

constitutional isomers

compounds with the same molecular formula but different connectivity (order of attachment of their atoms)

primary (1º) carbon

a carbon bonded to one other carbon

• creates/bonds to a 1º hydrogen

ssecondary (2º) carbon

a carbon bonded to two other carbons

• creates/bonds to a 2º hydrogen

tertiary (3º) carbon

a carbon bonded to three other carbons

• creates/bonds to a 3º hydrogen

quaternary (4º) carbon

a carbon bonded to four other carbons

• creates/bonds to a 4º hydrogen

cycloalkanes (rings)

general formula: C_nH_2n

• five- and six-membered rings are most common

bicycloalkanes

an alkane that contains two rings that share two carbon atoms

spiroalkanes

two rings that share one carbon atom

newman projection

the perspective of looking straight down at a C-C bond

• shows the front carbon as a point and the back carbon as a large circle behind it