1: the basics

Question 1

abbreviations for 1-6

Answer 1

1: meth
2: eth
3: prop
4: but
5: pent
6: hex

Question 2

abbrevs 7-12:

Answer 2

7: hep
8: oct
9: non
10: dec
11: undec
12: dodec

Question 3

nomenclature steps

Answer 3

1. longest continuous c chain = base name
2. number c’s - 1st sub lowest
3. name sub’s using C# and prefix di-, etc
4. list sub’s ALPHA – ignore numberical prefix and hyphenated prefixes BUT NOT iso or cyclo
5. more than one way to number chain? choose sub on lower C by alpha
6. multiple ways to come up with longest chain? pick one with most substituents

Question 4

when is the only time you use a numerical prefix to list alphabetically?

Answer 4

when a smaller chain is a substituent off the main chain — put it in parentheses, C1 of the sub chain is the C attached to the main chain, (2,3,4-trimethylpentyl) – in big name, you would use this as substituent and use tri for alpha

Question 5

IUPAC of isobutyl

Answer 5

2-methylpropyl

Question 6

IUPAC tertbutyl

Answer 6

dimethylethyl

Question 7

ether naming rules, common and IUPAC

Answer 7

common: name chains on either side of O, alphabetize them, add ether (ethyl methyl ether)

IUPAC: find longest chain and name ether as substituent (methoxyethane)

Question 8

what does n-(prop/but/etc)yl mean?

Answer 8

straight chain alkane (vs iso or tert, etc)

Question 9

amine

Answer 9

NH2, part of longest chain, butan-1-amine

Question 10

aldehydes

Answer 10

-al, dont need to number because at end of chain (chain - C double bond O and C also to H)

Question 11

carboxylic acid

Answer 11

-oic acid, dont need to number because it is at end with an OH (H in aldehyde; O- in -ate ion)

Question 12

ester

Answer 12

C1 = carbonyl C, single bond to other O

-longest chain is named at carboxylate ion (-ate) adn otherside of O comes 1st, ethyl butanoate

Question 13

amide

Answer 13

suffix: amide, C1 = carbonyl C, other side is NR2/NHR/NH2; ex- 3,N,N-trimethyl butyl if 5C chain with CH3 attached to the amide N and also to C3

Question 14

priority groups

Answer 14

1. carboxylic acids/derivs
2. aldehydes
3. ketones
4. alcohols
5. amine
6. alkynes/ene

Question 15

aromatics: benzene rings with attachments

Answer 15

1. toluene: CH3
2. benzoic acid: COOH
3. benzaldehyde: COH
4. phenol: OH
5. anilene: NH2
6. anisole: OCH3
7. styrene: ring-CH-pi bond-CHH
8. xylene: 2 CH3’s

Question 16

ortho, meta, para

Answer 16

ortho: next door
meta: 2 over
para: across

Question 17

electron domains (NOT MOLEC GEO) - includes bonding domain and lone pair

Answer 17

2: sp, 180, linear
3: sp2, 120, trigonal planar
4: sp3, 109.5, tetrahedral

Question 18

effect of lone pairs on molec geo

Answer 18

repulsion – bond angle lower than expected

Question 19

sigma vs pi

Answer 19

sigma: end to end overlap of orbitals, the hybrid orbital overlaps
pi: sideways overlap from p orbitals

Question 20

intermolecular forces:

1. H bond
2. dipole dipole

Answer 20

H-bond: super strong dip-dip; F-H/O-H/N-H required if pure BUT if in a protic solvent, only F, N, O needed (formaledyde, for example)

dip-dip: interaction between molecules with permanent dipole moment; larger dipole moment = larger force; only POLAR molecule

London: all molecules, larger = bigger, weak interaction due to transient dipole

Question 21

effects of IM on BP/MP/VP

Answer 21

higher IM force = higher BP and MP, lower MP

Question 22

effects of branching on MP and BP

Answer 22

more branching = lower BP bc less SA; higher MP bc locks into crystal lattice easier

Question 23

solubility ground rule

Answer 23

like dissolves like

Question 24

nucleophile

electrophile

Answer 24

nuc: e- donor; lone pairs e-; pi e-; (-) charge is better
electrophile: e- pair acceptor, (+) charge

Question 25

strength of nucleophiles, aprotic and protic

Answer 25

all of them get stronger as electronegativity decreases (because easier to donate e- if lower electronegativity) aprotic: stronger to left and up protic: H-bonds interact with the donor e- and reduce strength, but stabilizing effect is lower on bigger atoms, so strength increases with size in protic solvents (best is to the left and down)

Question 26

reaction intermediates - carbocation stability

Answer 26

3 > 2 > 1 > Me

Question 27

radical stability

Answer 27

3 > 2 > 1 > Me

Question 28

carbanion stability

Answer 28

me > 1 > 2 > 3

Question 29

resonance:

Answer 29

delocalization of e-, in more than one bonding position at once major resonance structure: most stable, more pi bonds (more bonding e- = lower energy), more (-) on more eneg atoms

Question 30

allylic carbon

Answer 30

C one away from pi, pi e- can move to it

Question 31

induction

Answer 31

makes carbocation less stable because it pulls (-) from (+), so a C-cat with 3 F's at end is less stable than H's makes carbanion more stable because it pulls (-) from (-), so C-anion with 3 F's more stable

Question 32

eneg highest to lowest

Answer 32

F O N Cl Br I --- C ---- H

Question 33

oxidation and reduction

Answer 33

oxidation: loss of e-, more bonds to eneg atom (more C-O), fewer bonds to electropositive atom (fewer C-H) reduction: gain e-, more bonds to epositive atoms (C-H), fewer to eneg (C-O)

Question 34

formula for saturated hydrocarbon

Answer 34

CnH(2n+2) 1 degree unsaturation = every 2H's missing from CnH2n+2

Question 35

unsaturation - how many degrees?

Answer 35

every 2 H's missing from CnH2n+2 is one degree unsaturation; pi bond or ring

Question 36

how do you solve a saturation problem given just the structure

Answer 36

count C's; determine # H's there should be for saturated molecule; count pi and rings to determine degree unsaturation; multiply that by 2 and subtract from the saturated number of H's to determine how many H's there actually are

Question 37

rules of saturation: O, N, X (halogen)

Answer 37

O: no change X: act as H N: add 1 more to # of H's needed for sat#

Question 38

acid vs base, BL defs

Answer 38

acid = H+ donor base = H+ acceptor

Question 39

base ranking overview

Answer 39

stronger acid = weaker conjugate base

Question 40

a more stable conjugate base means what?

Answer 40

stronger acid

Question 41

lower pKa means what

Answer 41

stronger acid (negative is strongest)

Question 42

5 base ranking rules -- CARDIO

Answer 42

C: charge A: atom R: resonance D-I: Dipole induction O: orbitals

Question 43

effect of C on acid/base

Answer 43

C = charge; (-) is stronger base, (+) is stronger acid

Question 44

effect of A on acid/base

Answer 44

A: atom 1. size - larger means more stable, so weaker base. smaller is stronger base. 2. electronegativity: more eneg is weaker because it stabilizes the charge **stonger up (smaller) and to the left (less eneg)

Question 45

effect of R on acid/base

Answer 45

R: resonance -- greater number and quality of resonance structures means more stable, means weaker base

Question 46

effect of D-I on acid/base

Answer 46

D-I: dipole induction; eneg atoms stabilize basic atom and make weaker base ***proximity and strength of electronegative atoms

Question 47

effect of O on acid/base

Answer 47

O: orbitals -- compare different carbons, sp>sp2>sp3 stability declines as you go from sp to sp3 electrons closer to nucleus (s) - lower energy, higher stability sp: 50% s, 50% p sp2: 33% s, 67% p sp3: 25-75

Question 48

how do you rank acids?

Answer 48

rank conjugate bases, weaker conjugate base means stronger acid

Question 49

exceptions to acid ranking --- there are 2

Answer 49

1. carboxylic acid is stronger than ammonia because of the resonance in the carboxylate (conj base of carb. acid) 2. carboxylic acid is stronger acid than phenol (2 resonance structures of carboxylate -- between 2 O's; stronger than 4 resonance structures of phenol between 3 C's and 1 O)