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Flashcards in O. Chem. Deck (377):
1

What are the 12 (1-12C) straight chain alkanes called

Methane
Ethane
Propane
Butane
Pentane
Hexane
Heptane
Octane
Nonane
Decane
Undecane
Dodecane

2

What is the formula for straight chain alkanes

C(n)H(2n)+2

3

What are the steps in naming organic compounds

1. Find the largest carbon backbone
2. Number the chain so the substituents are in the lower numbers
3. Name the substituents
4. Assign each substituent it's carbon number
5. List the substituents in alphabetical order (not counting the di,tri,tetra, sec, tert)(cyclo, iso and neo do count)
6. Assign (cis, trans, R, S, Z, E)

4

if there are two equally long carbon backbones, which one do you use for IUPAC naming

the more substituted one

5

What is a t-butyl substituent

- C(CH3)3

6

What is a neopentyl substituent

- CH2C(CH3)3
A t-butyl with a CH2 first

7

What is an isopropyl substituent

- C(CH3)2H

8

What is a sec-butyl substituent

An isopropyl with an extra carbon on one side

9

what is an iso butyl substituent

an isopropyl with an extra carbon in front

10

What do you do if there are more than one of a given substituent

use di-, tri-, tetra-

11

How do commas and dashes work in IUPAC naming

commas between two numbers, dashes between words and numbers

12

How do you start naming organic compounds where the largest carbon backbone is found in a ring

Assign C1 to be the MOST substituted carbon, and do the numbering so that the substituted carbons have the lowest numbers

13

What are olefins

alkenes

14

When double bonds are present how do you chose which carbon chain of equal length to use

the one with more double bonds (assuming it is tied for the longest chain with a double bond)

15

so what happens if you have a carbon chain of 5 with a double bond, or a carbon chain of 6 without the double bond

you use the 5 C chain with the double bond as your backbone

16

What does the term vinyl-mean

vinyl groups are monosubstituted ethylenes

17

What does the term allyl mean

allyl groups are monosubstituted propylenes (at the C3 location)

18

What is vinyl-chloride

a substituent ethylene with a chlorine at the C2 end

19

What is acetylene

ethyne

20

what is t-butyl bromide

C(CH3)3Br

21

Which has priority when numbering a chain an alcohol, a double bond, or a triple bond

Alcohol has priority

22

What are diols

molecules with 2 hydroxyl groups

23

what are vicinal molecules

molecules with hydroxyl groups on adjacent carbons

24

what are geminal molecules

molecules with 2 hydroxyl groups on the same carbon

25

What are ethers

ethers are 2 carbon chains that have an O inbetween them

26

what is an ether functional group called

alkoxy-

27

how are ethers named (IUPAC)

1. find the longest carbon chain with the ether
2. use the shorter chain as a substituent
3. number the ether
4. put -oxy- in before you name the carbon chain

28

how are common names of ethers derived

name the two alkyl groups in alphabetical order and add the word ether

29

What is an aldehyde

a carbonyl group with at least one H off of it

30

what is the suffix for aldehydes

-al

31

Where is the C1 in aldehydes

the carbonyl carbon

32

What is formaldehyde

methanal

33

What is acetaldehyde

ethanal

34

what is propionaldehyde

propanal

35

What is the suffix for ketones

one

36

how are ketones named

1. number the chain giving the ketone the lowest number possible

37

What is acetone

2 propanone

38

what is the suffix for carboxylic acids

- oic acid

39

where is the C1 for carboxylic acids

the carbonyl carbon

40

what is formic acid

methanoic acid

41

What is acetic acid

ethanoic acid

42

What is the suffix for amines

-amine

43

what is the substituent name for amines

amino

44

What do you do when a nitrogen is in the chain (like an ether)

you use N-(then name the shorter carbon substituent)

45

What are isomers

structures with the same molecular formula, but differ in structure

46

what are structural isomers

isomers with ONLY the same molecular formula

47

what are stereoisomers

isomers with the same molecular formula and connectivity

48

What are geometric isomers

compounds that differ in the position of substituents attached to a double bond

49

When do you use E or Z to name a double bond

when there are multiple substituents

50

how do you assign E and Z to double bonds

1. Find the highest atomic weight atom bonded to both sides of the double bond
2. if they are the same find the atomic weights bound to that one
3. if the higher priority are on the Zame Zide its Z
4. if the higher priority groups are on epposite sides its E

51

What is a chiral object

one that is not superimposable on its own mirror image

52

How do you assign R and S to stereocenters

1. Assign priority to the 4 groups based on atomic number
2. rotate it so #4 points away from you
3. If 1-2-3 is clockwise = R, if it is counterclockwise = S

53

what are the horizontal lines like in a fischer projection

sticking out of the page

54

enantiomers have identical chemical and physical properties with one exception...

optical activity

55

what does it mean when a compound is optically active

if it has the ability to rotate plan-polarized light

56

How is the rotation of light between two enantiomers related

they rotate light the same distance, but in opposite directions

57

what is an compound that rotates light to the right called

Dextrorotary (+)

58

What is a compound that rotates light to the left called

levorotary (-)

59

From which perspective do you assign directions to light rotation

from someone seeing the light approach them

60

What determines the amount of rotation caused by a compound to light

the number of molecules that the light wave encounters (concentration of the optically active compound and length of the tube through which the light passes)

61

what is the equation for specific rotation

specific rotation ([a]) =
observed rotation (a)/concentration*length

62

What is a racemic mixture

a mixture of equal parts of both the + and - enantiomers so that no optical activity occurs

63

how many possible stereoisomers are there for a molecule with n stereocenters

2n
(5 stereocenters = 10 possible stereoisomers)

64

What are enantiomers

nonsuperimposable mirror images

65

what are diastereomers

stereoisomers that are not mirror images

66

can enantiomers and diastereomers be seperated by physical means

no to enantiomers
yep to diastereomers

67

What are meso compounds

a compound with chiral centers but has a plane of symmetry
not optically active
superimposable mirror image

68

how do you remember what meso compounds are

MeSo
Mirror plane of Symmetry

69

What are conformaitonal isomers

compounds that differ only by the rotation about one or more single bond

70

What is the most stable conformation in newman projections

staggered or anti large groups
180 degrees away from each other
antiperiplanar

71

What is gauche in newman projections

the large groups are 60 degrees apart
higher in energy than staggered conformation

72

What is eclipsed in newman projection

when the bond is rotated so that the front and back groups all overlap

73

what is totally eclisped in newman projections

when the two largest groups are overlapped

74

what is the order of energy in newman projections from lowest to highest of the different orientation

1. stagered (anti)
2. gauche
3. eclipsed
4. totally eclipsed

75

What are the three types of strain that influence cyclic conformations

angle strain
torsional strain
nonbonded strain

76

what shape do cyclobutanes take

a puckered shape

77

what shape do cyclopentanes take

envelope shape

78

what are the three types of shapes cyclohexanes take (in order of stability)

1. chair
2. boat
3. twistboat

79

which is more stable large groups axial or equitorial

equitorial

80

What is a node in atomic orbitals

locations where the probability of finding an electron in the orbital is 0

81

how many nodes do s orbitals have

0

82

how many nodes do p orbitals have

1

83

how many nodes do d orbitals have

2

84

what is a molecular orbital

when two atomic orbitals combine

85

When does a bonding orbital occur

when the signs of the wave functions are the same
(when they are opposite it creates a non-bonding orbital)

86

what is a sigma bond

when two atomic orbitals overlap head to head

87

what is a pi bond

when two p-orbitals overlap in parallel fashion

88

What is a double bond (MO theory)

when both a sigma and a pi bond is formed between two atoms

89

What is a triple bond (MO theory)

when a sigma bond and two pi bonds are formed between two atoms

90

are pi bonds or sigma bonds stronger

sigma

91

are long or short sigma bonds stronger

short

92

what is an sp3

when one s orbital and 3 p orbitals are mixed to create 4 sp3 hybrid molecular orbitals

93

what is isobutane

C (CH3)3 H

94

What is neopentane

C(CH3)4

95

What is a primary, secondary, tertiary, and quaternary Carbon

primary = Bonded to 1 C
secondary = bonded to 2 C
tertiary = bonded to 3 C

96

What happens to boiling point, melting point, and density as chain length increases, and as branching increases

the longer the chain the higher the BP,MP, and Density are
the more branching there is the lower the BP, MP, and density are

97

What is free-radical halogentation

the addition of a halogen by substitution

98

what are the steps of free radical halogenation

1. Initiation
2. Propagation
3. Termination

99

How does initiation happen

Diatomic halogens are cleaved by heat or light creating two radicals

100

What are radicals

species with unpaired electrons
they are very reactive

101

How does propagation happen

1. The halogen radical reacts with an alkane, removing an H, Leaving a radical alkane
2. That radical alkane can react with a diatomic halogen creating an alkyl halide, and leaving another halogen radical

102

How does termination happen

two free radicals combine to form a stable molecule
can be 2 radical halides, 2 radical alkanes, or one of each

103

Where does bromine attack during free radical halogenation

bromine replaces a H on the most substituted C, because it is the most stable place for the radical

104

Where does chlorine attack during free radical halogenation

because the reaction is so fast it happens it is fairly random between carbons.

105

What are combustion reactions

The reaction of alkanes with O2 to form
H2O, CO2, and Heat

106

What is pyrolysis

the breaking down of a molecule by heat

107

what is another name for pyrolysis

cracking

108

What happens in pyrolysis

alkane C--C bonds are broken causing to alkyl radicals.
those radicals combine to form all sorts of alkanes

109

what is disproportionation

when an alkyl radical transfers a H to another radical producing an alkane and an alkene

110

What are nucleophiles

electron-rich species that are attracted to positively polarized atoms

111

what determines how good a nucleophile is if it has the same attacking group?

if they have the same attacking group, nucleophilicity is roughly correlated to basicity.
RO- > HO- > RCO2- > ROH > H20

112

what determines how good a nucleophile is if it doesn't have the same attacking group

the bigger the atom, the better it is as a nucleophile
CN- > I- > RO- > HO- > Br- > Cl- > F- > H20

113

what determines how good a nucleophile is in aprotic solvents

it is directly related to bascity
F- > Cl- > Br- > I-

114

What determines the quality of leaving groups

weak bases make the best leaving groups
I- > Br- > Cl- > F-

115

What is the mechanism of Sn1 reaction

1. dissociation of a molecule into a carbocation and a good leaving group
2. nucleuophilic attack on the carbocation

116

Where will Sn1 reactions occur the most

at the most substituted carbon

117

what is the slow step in an Sn1 reaction

the dissociation of a molecule into the carbocation

118

what determines the rate of Sn1 reactions

the concentration of the original molecule (not the concentration of the nucleophile

119

what things can increase the rate of Sn1 reactions

1. highly substituted carbons
2. highly polar-protic solvents
3. good leaving groups (weak bases)

120

What is the mechanism of an Sn2 reaction

1. nucleophile attacks the carbon opposite to the leaving group, bond strength shifts from the LG to the Nu. and the leaving group leaves

121

what does the nucelophile of an Sn2 reaction need to be like

strong and not sterically hindered

122

what determines the rate of Sn2 reactions

both the substrate, and the Nu

123

What order is an Sn2 reaction

2nd order

124

What does Sn1 reactions do to chirality

becuase it goes through a planar carbobation, it will produce two racemic products

125

What does an Sn2 reaction do to chirality

it keeps it chiral but flips it

126

what is the equation for finding double bond equivalents (degree's of unsaturation)

N = 1/2 (2n+2-m)

127

do cis or trans alkenes have higher boiling/melting point

trans-alkenes have a higher melting point (symmetry)
cis-alkenes have a higher boiling point (polarity)

128

what is one physical difference between internal and external alkenes

internal alkenes have a higher boiling point than terminal (external boiling points)

129

What is another name for an E1 reaction

unimolecular elimination

130

what is the mechanism for E1 reactions

1. Leaving group leaves creating a carbocation
2. a base removes a proton and a double bond is formed

131

What determines the rate of E1 reactions

only the rate of the substrate (it goes through a carbocation intermediate)

132

What factors favor E1

1. highly polar solvents
2. highly branched carbon chains (more substituted)
3. good leaving groups
4. weak nucleophiles

133

How do you favor E1 over Sn1

with high temperatures

134

What factors favor Sn1 reactions

1. highly polar protic solvents
2. highly branched carbon chains (more substituted)
3. good leaving groups
4. weak nucleophiles

135

what is another name for Sn2 Reactions

bimolecular elimination

136

What is the mechanism for Sn2 Reactions

1. a strong base removes a proton, causing the anti halide to leave, resulting in a double bond

137

What kind of double bond is favored in an Sn2 reaction

more substituted

138

What situations favor E2 over Sn2

1. highly substituted carbon chains
2. Strong bases favor E2 (weak bases favor Sn2)

139

What are stereospecific reactions

reactions that favor one stereoisomer over the others

140

What are reduction reactions to a double or triple bond

reactions that add hydrogen atoms to get rid of one of the bond

141

what does H2 / Pd do

reduction by syn addition of two hydrogen atoms

142

What things attack and add to double or triple bonds

electrophiles

143

How do HX's add to double bonds

1. a hydrogen is added to the less substituted side and a carbocation + is on the more substituted carbon
2. then the X- adds to the + carbon on the carbocation

144

What is markovnikov's rule

that the carbocation is on the more substituted carbon, and the H+ adds to the less substituted side

145

how do X--X's add to double bonds

1. The double bond attacks the X, displacing an X-, and forming a cyclic halonium ion (three atom ring with the X at the top)
2. the X- then attacks from below the ring, and the two X's end up being added anti

146

What can happen when adding XX's to a double bond, in a nucleophilic solution

the nucleophiles can add during the final step and have only one X added`

147

When can water be added to alkenes

under acidic conditions (H+/H20)

148

What happens when water is added to alkenes in acidic condition

1. the double bond is protonated according to Markovnikovs rule creating a carbocation
2. the carbocation reacts with water, and the water loses it's proton
3. final product is an OH added to the most substituted carbon

149

what happens in free radical addition of a double bond that is different from most reaction

it doesn't follow markovnikov's rule because the most stable radical is formed, not the most stable carbocation
(the halogen is added to a the less substituted carbon

150

What is hydroboration of a double bond (BH3/THF)

When BH3 is added to a double bond, then it is typically replaced with OH by (H2O2/-OH)

151

How does hydroboration of a double bond occur

1. A transition state is created where BH2 begins to add to the less substituted side, while the H adds to the other (Syn)
2. The bond between the BH2 and H breaks and a syn anti-markovnikov product is formed
3. Oh replaces the BH2

152

What does potassium permanganate KMnO4 do to double bonds

That depends on if is in a cold dilute solution or a hot basic solution

153

What does potassium permanganate KMnO4 do to double bonds in cold dilute solutions

they produce syn 1,2 diols
(Oh is added to syn to both sides of the double bond)

154

what does potassium permanganate KMnO4 do to double bonds is hot basic solutions

that depends on whether the alkene is terminal or not

155

what does potassium permanganate KMnO4 do to non-terminal double bonds is hot basic solutions

two molar equivalents of carboxylic acids are formed (Basically you cut the molecule at the double bond and create two carboxylic acids out of it, with the OH group where the double bond used to be)

156

what does potassium permanganate KMnO4 do to terminal double bonds is hot basic solutions

it will create a carboxylic acid and a CO2 molecule

157

What happens to a alkene that reacts with O3, CH2Cl2/(Zn/H2O)

the double bond is cleaved and turned into 2 carbonyls
(put two O's in the middle of the double bond and separate it)

158

What happens to an alkene that reacts with O3, Ch2Cl2/NaBH4, CH3OH

the double bond is split, just like in the other O3 reaction, but then the carbonyls are reduced to OH groups

159

what happens when alkenes are reacted with CH3CO3H and MCPBA

an epoxide is produced where the double bond was

160

what is another name for an epoxide

Oxirane

161

How is polymerization done to alkenes

with a radical

162

What happens when an alkene is reacted with (radical carbon chain), heat, and pressure

polymerization from the monomeric alkene

163

How are alkynes created

reacting a di-anti halogenic alkane with heat and a strong base

164

What happens when a terminal alkyne is reacted with n-BuLi

1. the hydrogen is removed creating an acetylide ion
2. the acetylide ion acts as a nucleophile and does nucleophilic displacement of a alkyl halide

165

What happens when you react alkynes with
H2,Pd/BaSo4
--------------------->
quinoline (lindlars catalyst)

two hydrogens are added cis to each other, and a double bond is retained

166

What are the two ways to reduce an alkyne and keep a double bond

H2,Pd/BaSo4
--------------------->
quinoline (lindlars catalyst)

Na,NH3 (liq)

167

What happens when you react an alkyne with Na, NH3 (liq)

two hydrogens are added trans to each other and a double bond is retained

168

what happens when you add Br2 to an alkyne

Br's are added trans to each other and the double bond is retained. or if there is enough Br2, the reaction will proceed until Br2 was added to each side twice.

169

what happens in free radical addition to triple bonds

the X (radical) and H are added to take it down to a double bond. Results in the trans isomer.

170

What happens when an alkyne is reacted with BH3

1. syn addition of H and BH2 occurs
2. then the BH2 is replaced with an H by acetic acid
3. a cis double bond is the final product

171

what happens when a terminal alkyne is reacted with
R2Bh
-------->
H2O2, OH-

an Oh is added to the terminal end, an H is added to the other side. Double bond is retained.
then it can tautomerize into an aldehyde

172

What happens to alkynes reacted with
1) KMnO4, OH-
---------------------->
2) H+

the triple bond becomes two carboxylic acids (the two carbons in the triple bond become the carbonyl carbons of the carboxylic acids)

173

What happens to alkynes reacted with
1) O3, CCl4
----------------->
2) H2O

the triple bond becomes two carboxylic acids (the two carbons in the triple bond become the carbonyl carbons of the carboxylic acids)

174

What is the electron rule for aromaticity

4n + 2 pi electrons in order for the molecule to be aromatic

175

what happens to aromaticity when you have $n pi electrons

you have an anti-aromatic structure (less stable)

176

What is toluene

a monosubstituted benzene with a CH3 group

177

what is phenol

a monosubstituted benzene with an OH group

178

what is analine

a monosubstituted benzene with an NH2 group

179

what is anisole

a monosubstituted benzene with an OCH3 group

180

What is benzoic acid

a monosubstituted benzene with an CO2H group

181

What is naphthalene

2 hooked benzene rings

182

what is anthracene

3 hooked benzene rings

183

what is pyridine

a benzene with a N(electron pair group in place of a C)

184

What is pyrrole

a 5 carbon ring, with two double bonds, and an NH(electron pair) group replacing one of the carbons

185

What happens when benzene is reacted with Br2 or Cl2 and FeCl3, FeBr3, or AlCl3

the benzene is halogenated once

186

what happens when benzene is reacted with F2 or I2

F2 usually leads to multisubstituted benzenes,
I2 usually doesn't react

187

What happens when benzene is reacted with
SO3/H2SO4
-------------------->
heat

suflonic acid is formed
(SO3H is monosubstituted to benzene)

188

What happens when benzene is reacted with
H2SO4
------------>
HNO3

NO2 is monosubstituted to benzene

189

what happens when benzene is reacted with a carbocation electrophile (carbonyl with a halogen) and a lewis acid (AlCl3)

Freidel-Crafts acylation
the carbocaiton electrophile is added to benzene

190

What kind of directors are electron donating groups

activating, Ortho/para directors

191

What are some activators

NH2, NR2, OH, NHCOR, OR, OCOR, R

192

What kind of directors are weakly electron withdrawing groups

deactivating, Otrho/para directors

193

what are some examples of weakly withdrawing groups

F, Cl, Br, I

194

What kind of directors are strongly electron withdrawing groups

deactivating, meta directors

195

what are some examples of strongly electron withdrawing groups

NO2, SO3H, Carbonyl compounds (COOH, COOR, COR, COH)

196

What happens when benzene is reacted with
H2, RH/C
-------------->
100 C

The benzene is reduced to cyclohexane
(can also be done with H2, Pd

197

what is m-cresol

an phenol with a methyl group added meta

198

what happens to boiling points of alcohol

they are higher than similar Hydrocarbons because they can H bond, this also makes them water soluble

199

What are the three reaction mechanisms for alcohol and ether reactions

1. Sn1/Sn2 nucleophilic substitution
2. Elecrophilic addition to a double bond
3. nucleophilic addition to a carbonyl

200

What is the oxidation/reduction continuum for primary alcohols

Primary alcohols aldehydes carboxylic acids
(reduction oxidation)

201

What is the oxidation/reduction continuum for secondary alcohols

secondary alcohols ketones
(reduction oxidation)

202

What happens in Sn1/Sn2 nulceophilic substitutions to alkyl halides

they can be turned into alcohols

203

What happens when an alkene is reacted with H2O

cis addition of H and OH

204

what happens to an carbonyl that is reacted with CH3MgBr

it is reduced to an alcohol

205

what happens when carbonyl groups are reacted with
1) LiAlH4
-------------->
2) H3O+

They are reduced to form alcohols

206

What happens when carbonyl groups are reacted with
1) NaBH4
--------------->
2) H3O+

The carbonyl group is reduced to form an alcohol

207

what is the difference in reduction between LiAlH4 and NaBH$

LiAlH4 is more powerful and can reduce carboxylic acids and esters, while NaBH4 can't

208

what happens when you add a para bromo analine to
HNO2
--------->
H2SO4

It turns into para bromo phenol

209

What happens when an alcohol is added to strongly acidic solutions (H2SO4)

it is dehydrated to alkenes

210

When alcohols are dehydrated in strong acid, what are the major and minor products

major = more substituted double bond
minor = less substituted double bond
(this is because the more subsituted went through a more stable carbocation)

211

is OH a good or bad leaving group

bad

212

what can be done to make OH a good leaving group

protonate it
convert it to tosylate
form an inorganic ester

213

What happens when you react an alcohol with HBr

the OH is protonated by HBr, then the Br- replaces the good OH2 + leaving group

214

What happens when you react an alcohol with tosyl chloride then NaI

the tosyl chloride reacts with the OH group making it a good leaving group, this is then replaced by I

215

What happens when you react an alcohol with SOCl2

The hydroxyl of the alcohol gets replaced by the Cl group

216

What happens when you react an alcohol with PBr3

The hydroxyl group of the alcohol gets replaced by Br

217

What happens when you react an alcohol with PCC

it converts primary alcohols to aldehydes
it converts secondary alcohols to ketones
it doesn't work on tertiary alcohols

218

What happens when you react an alcohol with
Na2Cr2O7
---------------->
H2SO4

it is oxidizes primary alcohols to carboxylic acids
it oxidizes secondary alcohols to ketones

219

what happenswhen you react an alcohol with
CrO3, H2SO4
---------------------->
acetone

primary alcohols are converted to carboxylic acids
secondary alcohols are converted to ketones

220

What is an ether

ROR

221

how are ether's named

small chain as the prefix, large chain as the suffix
____oxy_____

222

What is oxyethane

an 4 carbon ring with an O instead of a C

223

what is THF

a 5 carbon ring with an O instead of a C

224

how are ethers synthesized

reacting a metal alkoxide with a primary alkyl halide (becasuse for Sn2 to happen the alkyl halide cannot be sterically hindered)

225

what happens when you react RC-O- Na+ with R(1)-X

RC-O-R1 is formed via Sn2 (O- attacks R(1))

226

what happens when you react phenol and a primary alkyl halide with NaOH, H2O

you get a ether (phenol + alkane)

227

what happens when you react a alcohol with base and H+

you get internal Sn2, which forms an epoxide

228

what happens when you react a double bond with MCPBA

you get an epoxide formed

229

What is an ether

ROR

230

how are ether's named

small chain as the prefix, large chain as the suffix
____oxy_____

231

What is oxyethane

an 4 carbon ring with an O instead of a C

232

what is THF

a 5 carbon ring with an O instead of a C

233

how are ethers synthesized

reacting a metal alkoxide with a primary alkyl halide (becasuse for Sn2 to happen the alkyl halide cannot be sterically hindered)

234

what happens when you react RC-O- Na+ with R(1)-X

RC-O-R1 is formed via Sn2 (O- attacks R(1))

235

what is the prefix used when a ketone is a functional group

oxo-

236

what happens when you react a alcohol with base and H+

you get internal Sn2, which forms an epoxide

237

what happens when you react a double bond with MCPBA

you get an epoxide formed

238

What are peroxides, and how are they formed

they are ROOR's and they are formed by ethers reacting with O2 in the air

239

How is cleavage of ethers performed

in high temperatures, in the presence of HBr, or HI

240

which carbon is attacked in the opening of an epoxide

the more substituted C in the presence of acid
the least substituted C in the presence of base

241

What is the product of axid-catalysed epoxide openin

OH and halide on opposite carbons

242

what is the product of base-catalysied epoxide opening

OH and halide on the same carbon

243

what is the prefix used when aldehyde is a functional group

formyl-

244

what is the prefix used when a ketone is a functional group

oxo-

245

what is more polar, alcohols or ketones and aldehydes

alcohols, since they can H-bond

246

What are the three ways to make aldehydes and ketones

1. oxidation of alcohols
2. Ozonolysis of alkenes
3. Friedel-crafts acylation

247

What is an enol

when a ketone loses an alpha proton, the proton attaches to the O, and the double bond switches place

248

what are tautomers

two isomers that differ only in the placement of a proton

249

What happens when Nitrogen containing compounds react with aldehydes and ketones

the NH2R becomes =NR and water is lost

250

What is the most common form of addition to carbonyl's

nucleophilic addition to the carbonyl carbon. (if there are no good leaving groups the O gets protonated and thats it)

251

What is hydration of a carbonyl

when H2O acts as an Nu and attacks the carbonyl carbon. final product is a diol.

252

What is an acetal/hemiacetal

a hemi acetal is when an alcohol Nu adds to a ALDEHYDE, making an ether.
an acetal is when it does so twice

253

what is a ketal/hemiketal

a hemi ketal is when an alcohol Nu adds to a Ketone, making an ether.
an ketal is when it does so twice

254

What happens when a ketone is reacted with ROH

once it makes a hemiketal, twice it makes a ketal

255

What happens when an ylide is reacted with a ketone/aldehyde

1. it Nu attacks the carbonyl Carbon
2. it forms a cylcobutane with P and O
3. double bonds are created (O=P, C=C)

256

What happens when you add NH3 to a ketone/aldehyde

the NH2 nu adds to the reaction, then H2O is lost, and an imine forms

257

what is an imine

when N is double bound to a C

258

What happens when Nitrogen containing compounds react with aldehydes and ketones

the NH2R becomes =NR and water is lost

259

what happens when an aldehyde/ketone is reacted with
Hg(Zn)
----------->
HCl

the carbonyl is removed

260

How is aldol condensation done

1. in a base the aldehyde is converted to it' enol form
2 the enol form Nu attacks another aldehyde and adds to it.
3. the O- gets protonated to form an aldol

261

what does the alpha carbon substituent do to the acidity of carboxylic acids

withdrawing groups ( Cl, NO2) increase acidity
donating groups ( NH2, OCH3) decrease acidity

262

What does the wittig reaction do

converts aldehydes and ketones into alkenes

263

what happens to the witting reagent

it starts out as (C6H5)3P
added to CH3Br
= (C6H5)3P+CH3
added to base
= (C6H5)3P=CH2
Resonance
(C6H5)3P+---CH2- (ylide)

264

What happens when an ylide is reacted with a ketone/aldehyde

1. it Nu attacks the carbonyl Carbon
2. it forms a cylcobutane with P and O
3. double bonds are created (O=P, C=C)

265

What happens when you have an aldehyde reacted with KMnO4, CrO3, Ag2O

it is converted into a carboxylic acid

266

What happens when you react an aldehyde or ketone with LAH or NaBH4

it is reduced to an alcohol

267

What happens when you react an aldehyde or ketone with H2NNH2 ( wolff-kishner)

the NNH2 replaces the O,
in basic heated solutions the N2 will leave, and nothing will remain

268

what happens when an aldehyde/ketone is reacted with
Hg(Zn)
----------->
HCl

the carbonyl is removed

269

What can soaps do

solubilize nonpolar organic compounds in aqueous solutions becuase they have both a polar and a nonpolar end

270

What happens in Nu substitution in carboxylic acids

the Nu attacks and the negative O is formed just like normal. But then the OH is protonated and leaves when the C=O bond reforms
(simply the Nu replaces the OH)

271

what happens to the acidity of the H's in dicarboxylic acids

1. one carboxylic acid makes the other more acidic (electron withdrawing)
2. When that one loses it's proton, the - charge causes the 2nd carboxylic acid to be less acidic

272

where are beta dicarboxylic acids highly acidic

the alpha H's

273

what happens when you react aldehydes with KMnO4

you get a carboxylic acid

274

What happens when you react primary alcohols with KMnO4

you get a carboxylic acid

275

What is decarboxylation of a carboxylic acid

when a carboxylic acid loses CO2

276

what happens when you react an alkyl halide with
HCN, then in basic or acidic solutions

1. the CN will replace the halogen
2. the RCN will then dissociate into a carboxylic acid and ammonia

277

How is soap formation done

reacting a long chain carboxylic acid with KOH or NaOH

278

What can soaps do

solubilize nonpolar organic compounds in aqueous solutions becuase they have both a polar and a nonpolar end

279

What happens in Nu substitution in carboxylic acids

the Nu attacks and the negative O is formed just like normal. But then the OH is protonated and leaves when the C=O bond reforms

280

what happens when carboxylic acids are reacted with LAH

they are reduced to aldehydes, then they can be reduced to alcohols

281

How are esters formed

when they react with alcohols in acidic conditions

282

What happens when carboxylic acids are reacted with primary alcohols in acidic conditions

the alcohol Nu attacks and replaces the OH group, forming an ester

283

What happens when you react SOCl2 with a carboxylic acid

you get an acid chloride

284

What is decarboxylation of a carboxylic acid

when a carboxylic acid

285

what happens when an acyl chloride is reacted with H2/Pd/ BaSO4 or quinoline

it is reduced to an alcohol or an aldehyde

286

what is the order of reactivity between acyl halides, esters, amides, and anhydrides

1. Acyl Halides
2. Anhydrides
3. Esters
4. Amides

287

what are the acyl halides

carboxylic acid derivatives where the Oh has been replaced by a halide

288

how are acyl halides names

-yl halide

289

what happens when carboxylic acids are reacted with SOCl2, PCl3, PCI5, or PBr3

an acyl halide is produced

290

What happens when an acyl chloride is reacted with water

it undergoes hydrolysis, recreateing the carboxylic acid

291

what happens when an acyl chloride is reacted with an alcohol

an ester is created

292

what happens when anhydrides are reacted with benzene and AlCl3

you get a benzoketone and an carboxylate anion

293

what happens when an acyl chloride is reacted with a benzene and AICI3

the benzene replaces the halide

294

What is an anhydride

R-C=O__O__O=C-R

295

what happens when an acyl chloride is reacted with a carboxylate salt

the salt attacks the acyl chloride, the chloride leaves, the C=O bond is restored, and an anhydride is created

296

what can happen when a dicarboxylic acid is heated

it can react to form a cyclic anhydride

297

what happens when anhydrides are reacted with water

2 carboxylic acids are formed

298

what happens when you react an amide with
BrO- and then H2O

1) the Br adds to the N of the amide
2) the N loses it's H and forms water (nitrene)
3) the Br leaves, the N attaches to the R opposite (isocyanate)
4) the isocyante is hydrolized by H2O to make a primary amine and CO2

299

What happens when anhydrides are reacted with alcohols

an ester and a carboxylic acid are produced

300

what happens when anhydrides are reacted with benzene and AlCl3

you get a benzoketone and an carboxylate anion

301

What are amides

R-C=O__N-R__H (amino acid like)

302

How are amides named

1. -amide instead of -oic acid
2. anything attached to the N will be identified with the letter N

303

how are amides formed

1. reaction of acid chlorides with amines
2. Reaction of acid anhydrides with ammonia
(only primary and secondary amines work)

304

how is hydrolysis of amides done

in acidic conditions reacting with water

305

what is the hoffman rearrangement

amides are converted into primary amines

306

what happens when you react an amide with
BrO- and then H2O

1) the Br adds to the N of the amide
2) the N loses it's H and forms water (nitrene)
3) the Br leaves, the N attaches to the R opposite (isocyanate)
4) the isocyante is hydrolized by H2O

307

what happens when an ester is reacted with CH3CH2MgBr (grignard)

one equivalent with bulky groups = a ketone
more than one equivalent = tertiary alcohol

308

what is the suffix for esters

oate

309

how are esters synthesized

with alcohols and carboxylic acids (acid chlorides and anhydrides) under acidic conditions

310

what does hydrolysis of esters give you

an carboxylic acid and an alcohol

311

What is saponification

when fats (esters) as hydrolyzed under basic conditions to produce soaps.

312

What happens to soaps in acidic conditions

they are brought back to triacylglycerols

313

what are nitriles

C triple bonded to N

314

what is transesterificitaion

when an alcohol attacks an ester and just makes a new ester

315

What happens in claisen condensation

two ethyl acetates react in basic conditions to form
3-oxobutanoate

316

how is reduction of an ester done, and what does it produce

with LAH, and it produces two primary alcohols

317

what things have higher priority than amines in a carbon chain

OH and CO2H

318

what is the prefix/suffix for amine groups

-amine
amino-

319

What are carbamates

they are esters with the other side of the carbonyl being an N group

320

how are nitro compounds reduced to primary amines

Zn
------>
dil.HCl

321

what is the boiling point of amines like

between alkanes and alcohols

322

why do tertiary amines have lower bp's than primary or seconday amines

they can't H bond

323

What is nitrogen inversion

when nitrogen flips inside out and back quickly

324

What happens when you react alkyl halides with NH3

the NH group replaces the Halide, then if you add it to base it becomes an alkylamine

325

What does gabriel synthesis do

converts a primary alkyl halide into a primary amine without creating side products

326

What is used in gabriel synthesis

o-phthalic acid (converted to phthalamide by NH3) Which is a good Nu

327

how are nitro compounds reduced to primary amines

with
Zn
------>
dil.HCl

328

What happens when you react RNO2 with
Zn
------>
dil.HCl

the NO2 becomes NH2

329

what is the product of the hoffman elimination (exhaustive methylation)

you get the least substituted double bond (not like normal)

330

how can you get a primary amine from a nitrile

LAH or H+ and a catalyst

331

how can you get a amine from an aldehyde or a ketone

1. react aldehyde or ketone with NH3 (NR2H, NH2R) to produce an imine
2. react the imine with H2-Ni (raney nickel) to produce an amine

332

What happens when you react an aldehyde or ketone with an amine, then H2-Ni (raney nickel)

you get an amine

333

how do you get an amine from amides

LAH

334

what happens when you react an amide with LAH

you get an amine

335

What is the hoffman elimination (exhaustive methylation)

1. you react an amine with Excess MeI (this methylates the NH2 to N(CH3)3
2. react this with Ag2O and H2O, then heat, and the N(CH3)3 group leaves and creates a double bond

336

what is the product of the hoffman elimination (exhaustive methylation)

you get the least substituted double bond

337

When is simple distialltion used

to separate liquids that boil under 150 degrees and at least 25 degrees apart

338

When is vacuum distillation used

to separate liquids that boil over 150 degrees and at least 25 degrees apart

339

When is fractional distillation used

to separate liquids that boil with less that 25 degrees of separation

340

what is unique about fractional distillations

it has a fractional column with inert objects of large surface area. the liquids condense and re-evaporate all the way up the column, this causes the lower boiling point one to make it to the top much quicker than the other

341

What is agarose gel electrophoresis

its when you use gel electrophoresis to separate DNA and RNA based on size. (because it is negative you don't need SDS)

342

What are epimers

carbs that differ in configuration at only one carbon

343

What is isoelectric focusin

a way to separate things based on charge

344

what are the four bond vibrations that occur

symmetric bending
asymmetric bending
symmetric stretching
asymmetric stretching

345

what causes absorption of energy in IR to be recorded

a change in the net dipole

346

what type of vibration doesn't show in IR

symmtetric stretches

347

Do O2, Br2 show up on Ir

nope (no dipole)

348

How do you know the difference between L and R carbs

if the last OH is on the left, then it is an L, if it is on the right, then it is a D

349

how do you draw cyclic versions of fisher projected carbs

things on the right will be pointing down, those on the left will point up

350

What are anomers

things that differ at the anomeric carbon

351

what are alpha anomers and beta anomers

alpha anomers point down (axial)
beta anomers point up

352

which is more favored, alpha or beta anomers

beta (equitorial)

353

what happens when you react glucose with acid anhydride (CH3CO)2O and a base

all of the OH's become CH3CO2 groups
esters

354

what is a reducing sugar

a monosaccharide with an OH on C1

355

What is oxidation of glucose do

converts C1 from CHO to COOH
aldehyde to carboxylic acid

356

What happens when you react glucose with
Cu(OH)2
-------------->
benedict solution (tollens)

glucose C1 is oxidized from CHO to COOH

357

what happens when you react a hemiacetal (glucose) with an alcohol

you get an acetal (OR instead of OH) and a glycositic linkage

358

What is the linkage of cellulose

1,4 beta

359

what is the linkage of starch and glycogen

1,4 alpha (some 1,6 alpha)

360

What is the naturally occurring amino acid

L amino acids

361

What are the negative/acidic amino acids

aspartic acid
glutamic acid

362

What does it mean that aminoacids are amphoteric

they can be acids or bases

363

What is the henderson hasselbach equaiton

pH = pKa + log [conjugate base]/[conjugate acid]

364

When are amino acid bufferers best

within one pH unit of it's pKa or pKb

365

What are the nonpolar amino acids

alanine
valine
leucine
isoleucine
proline
phenylalanine
glycine
tryptophan

366

What are the polar (uncharged amino acids)

Methionine
Serine
Threonine
Cysteine
tyrosine
asparagine
glutamine

367

What are the basic amino acids (+)

arginine
lysine
histidine

368

how are peptides formed

condensation reactions

369

how are peptides cleaved

hydrolysis reactions

370

where does trypsin cleave proteins

the carboxyl end of arginine and lysine

371

where does chymotrypsin cleave proteins

carboxyl end of phenylanlanine, tyrosine, and tryptophan

372

how are peptides drawn

from the N-terminal to the C-terminal

373

what is keratin made of

many alpha helices

374

how many AA's away are the bonds between AA's in alpha helices

4

375

What are silk fibers made up of

beta sheets

376

what is the difference between cysteine and cystine

cystine is two bonded cysteines

377

why doesn't proline fit into alpha helices

causes a kink