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O-Chem > 1: the basics > Flashcards

1: the basics Flashcards

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1
Q

abbreviations for 1-6

A

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

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2
Q

abbrevs 7-12:

A

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

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3
Q

nomenclature steps

A
  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
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4
Q

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

A

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

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5
Q

IUPAC of isobutyl

A

2-methylpropyl

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6
Q

IUPAC tertbutyl

A

dimethylethyl

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7
Q

ether naming rules, common and IUPAC

A

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)

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8
Q

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

A

straight chain alkane (vs iso or tert, etc)

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9
Q

amine

A

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

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10
Q

aldehydes

A

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

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11
Q

carboxylic acid

A

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

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12
Q

ester

A

C1 = carbonyl C, single bond to other O

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

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13
Q

amide

A

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

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14
Q

priority groups

A
  1. carboxylic acids/derivs
  2. aldehydes
  3. ketones
  4. alcohols
  5. amine
  6. alkynes/ene
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15
Q

aromatics: benzene rings with attachments

A
  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
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16
Q

ortho, meta, para

A

ortho: next door
meta: 2 over
para: across

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17
Q

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

A

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

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18
Q

effect of lone pairs on molec geo

A

repulsion – bond angle lower than expected

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19
Q

sigma vs pi

A

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

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20
Q

intermolecular forces:

  1. H bond
  2. dipole dipole
A

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

21
Q

effects of IM on BP/MP/VP

A

higher IM force = higher BP and MP, lower MP

22
Q

effects of branching on MP and BP

A

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

23
Q

solubility ground rule

A

like dissolves like

24
Q

nucleophile

electrophile

A

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

25
Q

strength of nucleophiles, aprotic and protic

A

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)

26
Q

reaction intermediates - carbocation stability

A

3 > 2 > 1 > Me

27
Q

radical stability

A

3 > 2 > 1 > Me

28
Q

carbanion stability

A

me > 1 > 2 > 3

29
Q

resonance:

A

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

30
Q

allylic carbon

A

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

31
Q

induction

A

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

32
Q

eneg highest to lowest

A

F O N Cl Br I — C —- H

33
Q

oxidation and reduction

A

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)

34
Q

formula for saturated hydrocarbon

A

CnH(2n+2)

1 degree unsaturation = every 2H’s missing from CnH2n+2

35
Q

unsaturation - how many degrees?

A

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

36
Q

how do you solve a saturation problem given just the structure

A

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

37
Q

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

A

O: no change

X: act as H

N: add 1 more to # of H’s needed for sat#

38
Q

acid vs base, BL defs

A

acid = H+ donor

base = H+ acceptor

39
Q

base ranking overview

A

stronger acid = weaker conjugate base

40
Q

a more stable conjugate base means what?

A

stronger acid

41
Q

lower pKa means what

A

stronger acid (negative is strongest)

42
Q

5 base ranking rules – CARDIO

A

C: charge

A: atom

R: resonance

D-I: Dipole induction

O: orbitals

43
Q

effect of C on acid/base

A

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

44
Q

effect of A on acid/base

A

A: atom
1. size - larger means more stable, so weaker base. smaller is stronger base.

  1. electronegativity: more eneg is weaker because it stabilizes the charge

**stonger up (smaller) and to the left (less eneg)

45
Q

effect of R on acid/base

A

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

46
Q

effect of D-I on acid/base

A

D-I: dipole induction; eneg atoms stabilize basic atom and make weaker base

***proximity and strength of electronegative atoms

47
Q

effect of O on acid/base

A

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

48
Q

how do you rank acids?

A

rank conjugate bases, weaker conjugate base means stronger acid

49
Q

exceptions to acid ranking — there are 2

A
  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)

O-Chem (6 decks)

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