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MCAT > Organic Chem > Flashcards

Organic Chem Flashcards

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MCAT flashcards
1
Q

Dehydration of alcohol; mechanism?

A

Alkene; E1 or E2

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2
Q

Bond dissociation energies b/t 2 elements depend on…

A

hybridization

sp3-sp3 < sp3-sp2 < sp3-sp

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3
Q

Which hybridization has the highest bond dissociation energy?

A

sp (forms strongest bond ∴ releases the most energy when broken)

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4
Q

smaller atoms form stronger/weaker bonds?

A

smaller atoms form shorter bonds → shorter bonds are stronger bonds
∴ smaller atoms form stronger bonds

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5
Q

what type of alkene has the weakest bond? Why?

A 
unsubstituted alkene (all H)
- more substituted alkenes are more stable
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6
Q

What is characteristics of stronger bonds?

A
  • smaller substituents

- more EN substituents

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7
Q

What is unique about the amide C=O and C-N bond?

A

Can act as both SB and DB

  • shorter than normal C-N
  • longer than normal C=O
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8
Q

If amides were protonated, where would the proton go?

A

O

  • most basic site
  • resonance causes it to have partial neg charge
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9
Q

Hybridization of amide C and N

A

sp2 (due to DB formed on some resonance structures)

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10
Q

VSPER of amide

A

6 atoms are all coplanar (trig planar around C & trig planar around N)

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11
Q

EDG makes things more basic/acidic?

A

Basic

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12
Q

For something to be absorbed through respiration, it must be…

A
  • gas
  • liquid with low BP (high vapour pressure)
  • NO H-BONDING
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13
Q

What force (e.g. VDW, dipole, H-bond…) is experienced with interactions between 2 hydrophobic tails?

A

VDW

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14
Q

Rate sp, sp2, sp3 in terms of acidity

A

sp > sp2 > sp3

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15
Q

rate sp, sp2, sp3 in terms of basicity. Explain.

A

sp3 > sp2 > sp

DB draw electron density from the EN element

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16
Q

Which element tends to be the most basic?

A

N

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17
Q

Amines are very good…

A

nucleophiles

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18
Q

pKa + pKb =

A

14

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19
Q

aromatic amine

A

N must be in the aromatic ring

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20
Q

degrees of unsaturation:
N
Halogens
O

A

Pretend each is H and change number according to…
N = +1
Halogens = -1
O = 0

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21
Q

for IR, ↑cm-1 = __ energy. What does this mean?

A

↑
C=O is 1700
C-O is 1300
C=O bond has ↑energy ∴ stronger than C-O

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22
Q

Conjugation

A

alternating DB and SB

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23
Q

What is found around 1630 - 1600 cm-1?

A

Amide

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24
Q

what is the wavelength of ester, ketone, aldehyde?

A

ester: 1735
aldehyde: 1725
ketone: 1710

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25
Q

Stronger covalent bond = ____ H-bond

A

weaker

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26
Q

Weaker bonds show up as a broad/narrow peak in IR?

A

broad

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27
Q

NMR: upfield = ?, downfield = ?

A

upfield: shielded (0)
downfield: deshielded (10)

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28
Q

NMR for benzene

A

singlet at 7.0 ppm

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29
Q

NMR value: carbox acid

A

10-12 (broad)

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30
Q

NMR value: aldehyde

A

9-10

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31
Q

NMR value: aromatic H

A

7-8

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32
Q

NMR value: vinylic H

A

5-6

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33
Q

NMR value: alkoxy H

A

3.5-4

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34
Q

NMR value: alpha-H

A

2-2.5

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35
Q

NMR value: para-substituted ring

A

7.0 (dd)

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36
Q

which ring substitution has the least amount of peaks for NMR?

A

para

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37
Q

C-NMR: substitution vs. ppm

A

tertiary = lowest ppm (right)
primary = highest ppm (left)
3 > 2 > 1

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38
Q

Ester + NaOH

A

Ester is hydrolyzed to form

  • carboxylate
  • alkoxide

(Ester will dissolve in NaOH if refluxed)

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39
Q

Diols are axial-equatorial / axial-axial / equatorial-equatorial?

A

axial-axial / equatorial-equatorial both works, but cannot be axial-equatorial

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40
Q

H-bonding in diol occurs…

A

between O of one OH and H of other OH

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41
Q

dipolar

A

have dipole moment

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42
Q

optical isomer

A

rotate light in diff directions

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43
Q

geometrical isomer

A

differences in DB or ring structure

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44
Q

enantiomer

A

Non-superimposable mirror images

SR RS

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45
Q

Diastereomer

A

Non-superimposable non-mirror images

SR RR or SS

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46
Q

configurational isomer

A

identical bonds with different spatial arrangement of atoms

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47
Q

(+) polarity = CW or CCW?

(-) = ?

A

CW;

CCW

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48
Q

does having a chiral center mean the compound is optically active?

A

no, meso compounds have symmetrical, opposite chiral centers that cancel out any rotation

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49
Q

max number of stereoismers

A

2^n (n = number of chiral centers)

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50
Q

epimer

A

Deals with carbohydrates/sugars

- chirality changes at only 1 C

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51
Q

Anomer

A

special type of epimer where only difference in chirality is at anomeric C. Straight chain form would be identical.

e.g. a-D-glucose vs. B-D-glucose

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52
Q

Anomeric C

A

C in sugar that is bound to 2 oxygens

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53
Q

protic solvents hinder ____

A

nuc that can H-bond

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54
Q

What stereochemistry does SN2 prefer?

A

less hindered

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55
Q

reaction kinetics of SN2

A

second order

k[nuc][elec]

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56
Q

preferred solvent for SN2

A

polar, aprotic

e.g. ethers, ketones

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57
Q

A racemic mixture forms if SN_ reaction occurs and the reactant was ____

A

1;

chiral

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58
Q

how to distinguish between substitution and elimination?

A

elimination usually requires higher temperature

59
Q

physical properties of stereoisomers

A

enantiomers: identical physical properties
diastereomers: different physical properties

60
Q

physical property of racemic mixtures vs pure enantiomers

A

racemic mixtures are generally more stable

  • higher MP if solid
  • higher density
61
Q

which reaction happens faster: chlorination or bromination of alkane?

A

chlorination

62
Q

what happens to product formation when energy is added into a system?

A

less stable compounds form to absorb excess energy

63
Q

how to find number of structural isomers?

A

= number of unique C on alkane

64
Q

E2 conditions

A
  • basic

- high temperature

65
Q

E1 conditions

A
  • acidic

- high temperature

66
Q

regioselectivity deals with…

A

Markovnikov’s rule
The first substituent to be attached goes onto least substituted C
(e.g. Br would end up on more substituted C)

67
Q

Stereoselectivity deals with…

A

Syn vs Anti

Substituents likes to add to the least hindered face

68
Q

1,2 addition to conjugated diene is under ___ control

A

kinetic (product depends on most stable INTERMEDIATE)

69
Q

1,4 addition to conjugated diene is under ___ control

A

thermodynamic (product depends on most stable PRODUCT)

  • higher temperature allows less stable intermediate to form
  • rearrangement occurs to form more stable product
70
Q

is the transition state of Diels-Alder reaction aromatic?

A

yes

71
Q

the dienophile of a Diels-Alder reaction should have EWG/EDG attached to it to help the reaction proceed?

A

EWG

72
Q

conditions for fastest Diels-Alder reaction

A
  • EDG on diene
  • EWG on dienophile
  • Less bulky
73
Q

pericyclic reactions

A

repositioning pi & sigma bonds through formation of cyclic intermediate

74
Q

base unit of terpenes

A

isoprene (5C)

75
Q

monoterpene has __ C

A

10C

76
Q

which lab technique is used to separate terpenes?

A

steam distillation

77
Q

process of steam distillation

A
  1. pulp boiled
  2. oil from pulp is distilled
  3. distillate = water + terpenes
  4. separate using extraction techniques
78
Q

UV spectroscopy deals with…

A

pi bonds & conjugation

79
Q

effect of branching on BP

A

more branched = decrease BP

80
Q

alkoxide
good base?
good nuc?

A

C-O(-);
good base;
bad nuc

81
Q

are ketones & aldehydes protic or aprotic solvents?

A

aprotic

82
Q

is UV spectroscopy the same for aldehydes & ketones?

A

no, their pi-bonds are different

83
Q

ketals & acetals are formed/removed under ____ conditions

A

acidic

84
Q

hemiketals & hemiacetals are formed under ___ conditions, and removed under ____ condition

A

basic;

any

85
Q

is carbox acid a strong or weak acid?

A

weak

86
Q

saponification

A

ester -> carboxylate (R removed from OR -> O-)

in the presence of xs. H2O and KOH

87
Q

transesterification

A

exchange OR group on ester

88
Q

acid anhydride synthesis from carb axid is a ___ reaction

A

dehydration (add heat)

89
Q

are amides found in AA?

A

no, they are found in peptide chains! (peptide bond)

90
Q

relative reactivity:

acid halide, amine, ester, anhydride

A

acid halide > anhydride > ester > amine

91
Q

each new C-O bond increases oxidation state by ___

A

+2

92
Q

each new C-O bond increases oxidation level by ____

A

+1

93
Q

Grignard reactions always have __ in the product

A

OH (alcohol)

94
Q

when does grignard add twice?

A

when there is a LG on the C=O

95
Q

is grignard a base/acid (strength?)?

what type of solvent does it prefer?

A

strong base

polar aprotic solvent (Et2O)

96
Q

workup of grignard reactions use…

A

weak acid

97
Q

what is removed during aldol condensation?

A

H2O (O comes from C=O of a second aldehyde or ketone, H2 comes from CH3 on R group of first aldehyde/ketone)

98
Q

reactant and product of Claisen Condensation Reaction

A

R: ester + ester
P: B-ketoester

99
Q

biological application of aldol condensation

A

4th step of glycolysis (retro-aldol reaction)

100
Q

biological application of Claisen condensation

A

fatty acid synthesis

101
Q

transesterification is driven forward by…

A

Le Chateliers

102
Q

biological application of transesterification

A

fatty acid -> TG breakdown (saponification)

103
Q

iodoform test is used for…

A

methyl ketones

104
Q

methods in which aldehyde/ketone -> alkane

A

1) Clemmensen: Zn(Hg)/HCl [acidic]
2) Wolff-Kishner: NH2NH2 [basic]
3) SHCH2CH2SH + Raney Nickel [neutral]

105
Q

most transition metals have __ oxidation states. This means that they are good ____ agents

A 
\+;
reducing agents (go from 0 to some positive number = oxidized)
106
Q

Wolff-Kishner reaction is driven forward by…

A

removing N2

107
Q

protecting groups for:

1) aldehyde
2) ketone
2) alcohol

A

1) acetal
2) ketal
3) silyl ether

108
Q

match up:

anabolism, catabolism, reduction, oxidation

A 
anabolism = reduction
catabolism = oxidation
109
Q

anabolism usually takes places in the ___ while catabolism takes place in the ___

A

cytosol;

mitochondria (except glycolysis)

110
Q

NADH is responsible for…

A

reduction of aldehydes & ketones

111
Q

FADH2 is responsible for…

A

hydrogenation of pi-bonds

112
Q

I2/OH is used to test for…

Colour change?

A

methyl ketones

yellow ppt

113
Q

K2CrO4/H2SO4 is used to test for…

Colour change?

A

primary & secondary alcohols
aldehydes
(orange -> green)

114
Q

Br2/CCl4 is used to test for…

Colour change?

A

alkenes

brown -> clear

115
Q

IBr/CCl4 is used to test for…

Colour change?

A

unsaturated fats

purple -> clear

116
Q

derivative for aldehydes & ketones

A

2,4-dinitrophenylhydrazone

117
Q

derivative for alcohols

A

benzylesters

118
Q

derivative for osazones

A

sugars

119
Q

In mass spec, Cl has what ratio?

A

3:1

120
Q

in mass spec, Br has what ratio?

A

1:1

121
Q

Parent peak in mass spec

A

Peak of highest mass (furthest right on the y-axis)

122
Q

Base peak in mass spec

A

tallest peak in the whole graph (denoted as 100 for relative intensity; most intense)

123
Q

mutarotation

A

flip-flop between a and B forms of ring (straight chain form is intermediate)

124
Q

aldose ketose conversion occurs via ___ intermediate when acid catalyzed

A

enediol

125
Q

aldose ketose conversion occurs via ___ intermediate when base catalyzed

A

enolate

126
Q

glycosidic linkage is formed by a ___ reaction

A

hydrolysis

127
Q

which polysaccharides branch?

A

amylopectin & glycogen

128
Q

which polysaccharides are linear?

A

amylose & cellulose

129
Q

what type of interactions are found between cellulose molecules?

A

H-bonding

130
Q

____ linkages are usually responsible for branching in polysaccharides

A

1,6

131
Q

Nitric acid oxidizes glucose to…

Optically active?

A

glucaric acid;

Yes

132
Q

oxidized mannose =

Optically active?

A

mannaric acid;

yes

133
Q

oxidized galactose =

Optically active?

A

galactaric acid;

No (the COOH on both ends makes it meso compound)

134
Q

oxidized allose =

Optically active?

A

allaric acid;

No (the COOH on both ends makes it a meso compound)

135
Q

Benedict’s Test (Fehling’s solution)

A

Test for reducing sugars (e.g. aldehydes) vs. non-reducing sugars (e.g. ketones)
+ test: blue -> red (there is a reducing sugar present)

136
Q

Tollen’s Test

A

Test for aldehydes (distinguish between aldehyde & ketones)

+ test: silver mirror forms (when aldehyde present)

137
Q

Periodate oxidation

A

cleaves C-C bonds in sugar (will end up with a bunch of 1 C fragments)

  • terminal C gains 1 bond to O
  • internal C gain 2 bonds to O
138
Q

Killiani-Fischer synthesis

A

increase C chain of aldose by 1 (cyano group added)

139
Q

Ruff degradation

A

Remove 1 C from aldose (decarboxylation)

140
Q

Wohl Degradation

A

remove 1 C from aldose (lots of N intermediates)

141
Q

how to increase the length of aldose?

A

Killiani-Fischer synthesis

142
Q

How to decrease the length of aldose?

A

Ruff degradation & Wohl degradation

143
Q

what is the only oxidation step in glycolysis?

A

G3P -> 1,3 BPG

MCAT (4 decks)

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