haha gagi basta Flashcards
(111 cards)
1
Q
- the existence of molecules that have the same numbers of the same kinds of atoms (and hence the same formula) but differ in chemical and physical properties.
A
ISOMERISM
2
Q
Isomers that differ in connectivity are called _____ . They have the same parts, but those parts are attached to each other differently.
A
constitutional (sometimes structural) isomers
3
Q
are isomers that have the same composition (that is, the same parts) but that differ in the orientation of those parts in space
A
stereoisomers
4
Q
In a _____ , the front carbon is located at the intersection of the bonds to the three attached hydrogen atoms, and the back carbon is an exploded circle, with the attached bonds emanating from the circumference of the circle.
A
Newman projection
5
Q
Rotations about carbon-carbon bonds interconvert two equally energetic chair forms. This process is colloquially called a ____
A
ring “flip.”
6
Q
are chemical compounds that are often derived from alkanes that contain one or more halogens
A
Alkyl halides also called haloalkanes or halogenoalkanes
7
Q
In this type of haloalkanes, the carbon which is bonded to the halogen family will be only attached to one other alkyl group. It doesn’t matter how much bulky group is attached to it.
A
Primary Alkyl Halide
8
Q
In this type of haloalkanes, the carbon atom which is bonded with the halogen atom is joined directly to the other two alkyl groups which can be the same or different
A
Secondary Alkyl Halide
9
Q
In this type of haloalkanes, the carbon atom which carries the halogen atom is directly bonded to three alkyl group. This alkyl group maybe with a combination of the same or different.
A
Tertiary Alkyl Halide
10
Q
• Due to greater polarity and greater molar mass as compared to parent hydrocarbon, the intermolecular force of attraction is ____ in halogen derivatives.
A
stronger
11
Q
• The attraction gets stronger as the size and number of electrons ___.
A
increases
12
Q
• The haloalkanes are ____ soluble in water.
A
less
13
Q
• They are used as solvents for relatively non-polar compounds and as starting materials for the synthesis of a wide range of organic compounds.
A
Uses of alkyl halide
14
Q
- Previously used as refrigerants and propellants.
* They are also used in fire extinguishers
A
alkyl halides
15
Q
Structural (constitutional) isomers have the same molecular formula but a different bonding arrangement among the atoms.
A
STEREOISOMER
16
Q
have identical molecular formulas and arrangements of atoms.
A
Stereoisomers
17
Q
They differ from each other only in the spatial orientation of groups in the molecule.
A
sterioisomers
18
Q
- They differ in connectivity
* They have the same parts, but those parts are attached to each other differently.
A
CONSTITUTIONAL ISOMERS
19
Q
- compounds of identical molecular formula but which have different functional groups.
A
Functional isomers:
20
Q
Stereoisomers have the same atomic connectivity but differ in the spatial arrangement of the constituent atoms.
A
STEREOISOMERISM
21
Q
- involves the study of the relative spatial arrangement of atoms that form the structure of molecules and their manipulation.
A
STEREOCHEMISTRY
22
Q
focuses on stereoisomers, compounds that have same molecular formula and sequence of bonded atoms (constitution), but differ in the three-dimensional orientations of their atoms in space.
A
STEREOCHEMISTRY-
23
Q
Stereochemistry is also called ___ because stereo means____
A
3D Chemistry
three dimensionality
24
Q
are stereoisomers that are non-superimposable on their mirror images.
A
ENANTIOMERS
25
are stereoisomers that are not mirror images of each other - they are stereoisomers that are not enantiomers.
Diastereomers
26
Molecules that can exist as enantiomers are said to be ___; they are non-superimposable on their mirror images.
chiral
27
is a necessary and sufficient condition for the existence of enantiomers.
Chirality
28
An object is __ if its mirror image is different from the original object.
chiral
29
Mirror images that can be superposed are .
achiral (not chiral)
30
When the images can be superimposed, the compound is .
achiral
31
An asymmetric carbon atom is the most common example of a
chirality center.
32
A ) is any atom at which the interchange of two groups gives a stereoisomer.
stereocenter (or stereogenic atom
33
A molecule that has a plane of symmetry is
achiral.
34
are compounds that contain either double bonds or else ring structures that prevent functional groups from freely rotating around a chemical bond
GEOMETRIC ISOMERS
35
In a ___ isomer, the functional groups are on the same side of a chemical bond.
cis
36
In a trans isomer, the functional groups are on ___ sides of a bond.
opposite or transverse
37
A carbon atom bonded to four different groups is called a
tetrahedral stereogenic center, asymmetric center, or chirality centre.
38
are NOT ISOMERS they are different arrangements of the SAME MOLECULE.
Conformations
39
The conformation of a molecule containing two tetrahedral atoms linked together can be represented as a
"Newman" or as sawhorse projections.
40
In the _________the molecule is viewed along the axis of a rotatable bond.
Newman projection
41
_____are very similar to Newman Projections, but are used more often because the carbon-carbon bond that is compressed in a Newman Projection is fully drawn out in a ____
Sawhorse Projections
42
_______: a conformation about a carbon-carbon single bond where the atoms on one carbon are as far apart from atoms on the adjacent carbon
Staggered conformation
43
a conformation about a carbon-carbon single bond where atoms on one carbon are as close as possible to the atoms on the adjacent carbon
Eclipsed conformation:
44
The force that opposes the rotation of one part of a molecule about a bond while the other part of the molecule is held fixed
Torsional Strain
45
It Determines the Energy Difference
Electron Pair Repulsions
46
The torsional strain between eclipsed and staggered ethane is approximately
2.9 kcal/mol
47
Longer distance, repulsions are
Shorter distance means _____repulsions for Eclipsed
less; larger
48
- Description given to two substituents attached to adjacent atoms when their bonds are at 180° with respect to each other.
Anti
49
- Description given to two substituents attached to adjacent atoms when their bonds are at 0° with respect to each other.
Syn
50
- Description given to two substituents attached to adjacent atoms when their bonds are at 60° and 300° with respect to each other.
Gauche
51
The _____ form is less stable than the anti form by 0.9 kcal/ mol due to _____ between the two methyl groups.
gauche; steric hindrance
52
-Destabilization due to the repulsion between the electron clouds of atoms or groups. Groups try to occupy some common space.
Steric
53
- Destabilization due to the repulsion between pairs of bonds caused by the electrostatic repulsion of the electrons in the bonds. Groups are eclipsed.
Torsional
54
- Destabilization due to distortion of a bond angle from it's optimum value caused by the electrostatic repulsion of the electrons in the bonds
Angle
55
. The six axial bonds, one on each carbon, are parallel and alternate up-down.
Axial bonds
56
The method of unambiguously assigning the handedness of molecules
Cahn-Ingold-Prelog Notation
57
Assign sequence priorities to the four substituents by looking at the atoms attached directly to the chiral center.
The Sequence Rule
58
Fischer Rules
►Carbon chain is on the ____ line.
►Highest oxidized carbon is at ___ . Rotation of 180° in plane doesn't
change molecule.
Rotation of ___ is NOT allowed
vertical; top; 90°
59
Enantiomers have ___ configurations at each corresponding chiral carbon.
► Diastereomers have some ____ configurations.
opposite
| matching, some opposite
60
These compounds have a plane of symmetry.
Meso compounds
60
Meso compounds are ___ even though they have chiral centers
achiral
61
Some molecules have structures that cannot be shown with a single representation. In these cases we draw structures that contribute to the final structure but which differ in the position of the π bond(s) or lone pair(s)
■ Such a structure is delocalized and is represented by ___
Resonance; Resonance forms
62
A structure with resonance forms does not alternate between the forms
Instead, it is a hybrid of the resonance forms, so the structure is called a
resonance hybrid
63
In the , the actual structure, all its C-C bonds are equivalent, midway between double and single
resonance hybrid
64
The resonance bond is ____ than a single bond and larger than a .
shorter ; double bond
65
Rules for Resonance Structures
■ All structures must be valid _____.
☐ There must be extra ____, and somewhere to move them.
The true structure of a molecule is a ____ or average of the individual resonance structures.
■ It does not quickly shift back and forth between them.
Resonance structures increase the _____of the molecule compared with molecules lacking resonance structures.
■ More structures =
```
Lewis Structures.
electrons
hybrid
overall stability
more stability.
```
66
Relative Stability of Resonance Structures:
■ Structures in which all atoms (except hydrogen) have a ____ are especially stable and make larger contributions to the hybrid.
■ Structures with ___ formal charges contribute more.
complete octet
| fewer and lower
67
Relatively few molecules formed with nonmetals contain odd numbers of electrons.
■ These examples usually involve N.
These are not very stable.
Odd Electron Molecules
68
The difference between the number of valence electrons on the free atom and the number of valence electrons assigned to the atom in the molecule.
Formal Charge
69
The oxygen atom in the structure has two lone pairs.
Carbonyl group
70
____bond is shorter, stronger, and more polar than C=C bond in alkenes.
C=O
71
any of a class of organic compounds characterized by the presence of a carbonyl group in which the C atom is covalently bonded to an O atom (double bonds)
Ketones
72
Properties of ketones
-Ketones are _____ acceptors.
- Ketones are not usually ___ and cannot hydrogen-bond to themselves.
- Because of their inability to serve both as hydrogen-bond donors and acceptors, ketones tend not to "self-associate" and are ___ than alcohols and carboxylic acids of comparable molecular weights
- Oxygen is more electronegative than carbon (3.5 vs 2.5) and, therefore, a C=O group is ___
- Ketones are polar due to this C-O bond and therefore have ____ than hydrocarbons making their boiling points ____
```
hydrogen-bond
hydrogen-bond donors
more volatile
polar
stronger intermolecular forces/higher.
```
73
BOILING POINT
More polar, so higher boiling point than comparable ___
Cannot H-bond to each other, so lower boiling point than comparable ___
alkane or ether.
| alcohol.
74
Acid-base properties of ketones
| -C-H bonds ____ to the carbonyl in ketones are ___ (pK, 20) than the C-H bonds in __ (pK,= 50).
adjacent
more acidic
alkane
75
The ____ of the a-hydrogen also allows ketones and other carbonyl compounds to react as ____ at that position, -Ketones are also ____
acidity; nucleophiles; weak bases,
76
female sex hormone- ,
male sex hormone-, and
adrenal hormone-
in musk deer,
progesterone
testosterone
cortisone
muscone
77
-any of a class of organic compounds in which a carbon atom shares a double bond with an oxygen atom, a single bond with a hydrogen atom, and a single bond with another atom or group of atoms
Aldehyde
78
Properties of Aldehydes
BOILING & MELTING POINTS
O The melting and boiling points of carbonyl-containing compounds are considerably ____than hydrocarbons
higher
79
INTERMOLECULAR INTERACTION AND SOLUBILITY
• Lone pair of electrons on oxygen of carbonyl can accept a hydrogen bond from ___.
Aldehyde is ____ in water.
O-H or N-H
| miscible
80
PHYSICAL STATES
* Formaldehyde (HCHO) is a ___ under standard conditions,
* Acetaldehyde (CH,CHO) boils at about ____.
Other aldehydes, except those of high molecular weight, are ___ under ordinary conditions..
gas
room temperature
liquids
81
any of a class of organic compounds in which a carbon (C) atom is bonded to an oxygen (0) atom by a double bond and to a hydroxyl group (-OH) by a single bond.
CARBOXYLIC ACIDS
82
Properties of Carboxylic Acid
___molecular weight carboxylic acids
taste
aromas
Low
Sharp, sour
Unpleasant
83
are named according to the same system as other organic compounds. othe suffix -oyl chloride is added to the stem used to o indicate the number of carbon atoms in the longest chain within the molecule.
Acid Chlorides/Acyl Halide
84
name of the parent acid, and replace the word "acid" by "anhydride". "Anhydride" simply means "without water". ethanoic acid form@ethanoic anhydride propanoic acid forms propanoic anhydride
Acid Anhydrides
85
are named as if the alkyl chain from the alcohol is a substituent.
Esters
86
This is followed by the name of the parent chain from the carboxylic acid part of the ester with an -e remove and replaced with the ending-oate.
esters
87
are named by changing the name of the acid by dropping the -oic acid or -ic acid endings and adding -amide.
Amides
88
• Nitriles used to be known as ____; the smallest organic nitrile is ____,
cyanides; ethanenitrile
89
The prefix cyano- is used interchangeably with the term nitrile in literature to refer to the functional group.
Nitriles
90
contain an OH group connected to a a saturated C (sp³) They are important solvents and synthesis intermediates
Alcohols
91
, is a common solvent, a fuel additive, produced in large quantities
Methanol, CH,OH, called methyl alcohol
92
alcohol, is a solvent, fuel, beverage
Ethanol, CH,CH₂OH, called ethyl
93
Methyl (C has __),
Primary (1°) (C has ___),
secondary (2°) (C has ____),
tertiary (3°) (C has ___),
3 H's
two H's, one R
one H, two R's
no H, 3 R's
94
contain an OH group connected to a carbon in a benzene ring
Phenols
95
Alcohols and phenols have much ____ boiling points than similar ____
Alcohols Form ___
A __ polarized OH hydrogen atom from one molecule oxygen atom of another molecule is attracted to a ___ of electrons on a negatively polarized
higher; alkanes and alkyl halides
Hydrogen Bonds
positively ;lone pair
96
Alcohols and Phenols are Weak ___
Brønsted Acids
97
are about as acidic as water
groups make an alcohol a weaker acid The more easily the alkoxide ion is solvated by water the more its formation is energetically favored Steric effects are important
Simple alcohols
| Alkyl
98
Electron-withdrawing groups make an alcohol a stronger acid by stabilizing the conjugate base
(alkoxide)
99
are bases used as reagents in organic chemistry
NaNH2, and Grignard reagents (RMgX) Alkoxides
100
Phenols (pK -10) are much ___ than alcohols (pK16) due to ____ of the phenoxide ion
Phenols react with ___ solutions (but alcohols do not), forming soluble salts that are soluble in dilute aqueous
A phenolic component can be separated from an organic solution by ____into basic aqueous solution and is __ after acid is added to the solution
more acidic; resonance stabilization
NaOH
extraction; isolated
101
Phenols with an electron-donating substituent are ___ because these substituents concentrate the charge
less acidic
102
Hydroboration/oxidation: syn, non-Markovnikov hydration
| ______: Markovnikov hydration
Oxymercuration/reduction
103
- a reaction that involves the replacement of one molecule or an atom of a compound with another molecule or an atom.
a reaction wherein the functional group of one chemical compound is substituted by another group.
SUBSTITUTION REACTIONS
104
are actually Lewis acids & Lewis bases
Electrophiles & nucleophiles
105
+charged & therefore e- loving; looking for an e-rich nucleophile E acids
Electrophiles
106
e-rich (sometimes -) & looking for an e- seeking electrophile
Nucleophile
107
: the group removes a proton and takes it away
| : attacks the other reactant & is added to it
Base
| Nu
108
A common theme of organic reactions is _____ oa nucleophile uses its electron pairs to attack an electrophile, a chemical with low electron density.
Nucleophilic Attack:
109
The ___, more __ shape of the sp alkyne orbitals places electrons closer to the nucleus.
The more ___ electrons are held to the nucleus, the __they are pulled toward hydrogen atoms they are bonded to.
___are therefore better acids than___ becuase their hydrogen are ____bound.
shorter; spherical
tightly; less
Alkynes; alkenes and alkanes; less tightly
110
are compounds that contain either double bonds or else ring structures that prevent functional groups from freely rotating around a chemical bond.
GEOMETRIC ISOMERS
