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Organic chemistry > Part 1 > Flashcards

Part 1 Flashcards

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1
Q

Formal charge formula

A

FC = valence e- - bonding e-

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2
Q

Formal charge:

        | 1.     -  C  -
        |

        \+ 2.     -  C -
        |
A

0 and 1

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3
Q

Difference between isomers and resonance structure

A

Isomers - different arrangement of atoms and electrons

Resonance structure - differ in arrangement of electrons

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4
Q

The only accurate representation of resonance stabilized compounds, due to delocalized e- density

A

Resonance hybrid

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5
Q

Trend for bond length in periodic table

A

/

\/

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6
Q

Which is stronger?

Sigma bond or pi bond

A

Sigma

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7
Q

Label each as Ionic or covalent

A. NaI
B. BrCl
C. HCl
D. CH3NH2
E. NaOCH3
A 
A. Ionic
B. Covalent
C. Covalent
D. Covalent
E. Ionic
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8
Q

The ____ the pKa, the stronger the acid

A

Lower

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9
Q

Acidity in periodic table

A

—->
|
\/

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10
Q

Arrange in increasing bond length

C-H
O-H
N-H

A

BCA

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11
Q

Arrange in decreasing bond length

HF
HCL
HBR

A

HBR>HCL>HF

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12
Q

Steps in drawing Lewis structure

A
  1. Count valence e-
  2. Count e- if there are no bonds (octet)
  3. Count bonded e- (bond e- = 1/2(step 2 - step 1)
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13
Q

Lewis acid

A

e- pair acceptor

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14
Q

Lewis base

A

e- pair donor

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15
Q

Bronsted-Lowry base

A

Proton acceptor

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16
Q

The stronger the acid, the _____ the conjugate base

A

Weaker

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17
Q

In proton transfer reactions, equilibrium favors the _____ acid and _____ base

A

Weaker, weaker

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18
Q

Factors that determine acidity (4)

A
  1. Element effects
  2. Inductive effects
  3. Resonance effect
  4. Hybridization effects
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19
Q

In hybridization effect in acidy, the acidity of HA increases as the percent s character of A _____.

A

Increases

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20
Q

Arrange in increasing acidity

sp
sp2
sp3

A

sp3 sp2 sp

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21
Q

What is the conjugate acid of each base

  1. H20
  2. NH2
  3. HCO3
A
  1. H20 - H30
  2. NH2 - NH3
  3. HCO3 - H2CO3
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22
Q

Rank in order of increasing acidity

NH3, H2O, HF

A

NH3 H2O HF

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23
Q

Rank the ff in order of increasing acidity

HBr, HCl, HF

A

HF < HCl < HBr

Acidity increases down a column

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24
Q

Difference between lewis acid and bronsted-lowry acid

A

A lewis acid is an electron pair acceptor and usually contains a proton of an unfilled valence shell of electrons. A bronsted lowry acid is a proton donor and must contain a hydrogen atom.
(All BL acids are lewis acids, though the reverse may not be true)

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25
Q

Classify each species as a lewis acid, bronsted-lowry or neither

H3O+
Cl3C+
BCl3
BF4-

A

H3O+ both
Cl3C+ lewis acid
BCl3 lewis acid
BF4- neither

26
Q

Types of intermolecular forces of attraction (4)

A
  1. Van der Waals (LDF)
  2. Dipole-dipole
  3. Hydrogen bonding
  4. Ion-ion
27
Q

Cause of dipole-dipole and give examples

A

It is due to the interaction of permanent dipoles

Ex. (CH3)2C=O, H2O

28
Q

This is due to the electrostatic interaction if an H atom in an OH, NH, HF bond with another N, O or F atoms

A

H-bonding

29
Q

Give example of ion-ion IMFA

A

NaCl, LiF

30
Q

Van der waals or LDF is due to

A

Due to the interaction of temporary dipoles

Ex. All inorganic compounds

31
Q

Arrange IMFA in increasingr strength

A

VDW-Dipole dipole-Hydrogen bonding-Ion Ion

32
Q

Relation: Boiling Point and IMFA

3

A
  • Stronger the forces the higher the BP
  • for similar functional groups, the larger the area, higher BP
  • more polarizable atoms, the higher the BP
33
Q

Relation: Melting point and IMFA

A
  • for compounds comaparable in MW, the stronger the forces the higher the MP (same as BP)
  • with compounds with similar functional group, the more SYMMETRIC, the higher MP
34
Q

Rank in increasing strength of IMFA

A. CH3NH2
B. CH3CH3
C. CH3Cl

A

BCA

35
Q

Rank the compounds in order of increasing strength of IMFA

A. CH3Br
B. CH3I
C. CH3Cl

A

CAB

36
Q

Rank the compounds in order of increasing strength of IMFA

A. NaCl
B. CH3OH
C. CH3Cl

A

CBA

37
Q

Rank in increasing boiling point

A. CH3(CH2)4I
B. CH3(CH2)5I
C. CH3(CH2)6I

A

As is (high SA,high BP)

38
Q

Rank the compounds in order of increasing melting point

A. (CH3)2CHOH
B. (CH3)3CH
C. (CH3)2C=O

A

BCA

39
Q

Rank the compounds in order of increasing melting point

A. CH3F
B. CH3Cl
C. CH3I

A

ABC

40
Q

Explain why benzene has a lower boiling point but much higher melting point than toluene

A

BP is solely determined by the strength of IMFA. Since bezene has a smaller size, it has less SA and weaker VDW interactions and therefore a lower boiling point than toluene. The increased MP for benzene can be explained by symmetry

41
Q

Rank the compounds in order of increasing water solubility

A. (CH3)3CH
B. CH3OCH2CH3
C. CH3CH2CH2CH3
D. CH3CH2CH2OH

A

CABD

(For A: this nonpolar, hydrophobic molecule is mole compact making it more H20 soluble than its straight chain isomer

42
Q

Molecular formula for alkanes

A

CnH2n+2

*cycloalkanes CnH2n

43
Q

Alkane conformations can be classified as ____, ____, ____ or ____ depending on the relative orientation of the groups on adjacent carbons

A

staggered, eclipsed, anti or gauche

44
Q

Staggered dihedral angle

A

60 degrees

45
Q

Two reperesentation of conformers

A

Sawhorse and newman

46
Q

Two types of isomers and its definitions

A

Constitutional isomer - isomers that differ in the way the atoms are connected to each other

Stereoisomer - isomers that differ only in the way atoms are oriented in space

47
Q

of carbons gas, liquid, solid phase

A

Gas C1-C4
Liquids C5-C17
Solids >C18

48
Q

Fuel for get engine

A

Kerosene (C9-C16)

49
Q

Aka asphalt

A

Bitumen

50
Q

Bromination - alkane

A

3* most stable

51
Q

Two types of stereoisomers and its definition

A

Enantiomer - stereoisomer that are nonsuperimposable mirror images of each other

Diastereoisomers - stereoisomer that are not mirror images of each other

52
Q

Difference of chiral and achiral

A

Chiral- must have 4 different groups attached
*chirality - with no plane of symmetry

Achiral - plane of symmetry

53
Q

Ability of a compound to rotate plane-polarized light

A

Optical activity

54
Q

A mixture having equal mixture of two enantiomers

A

Racemic mixture

55
Q

Meso compunds are

A

Achiral with plane of symmetry

56
Q

Diastereoisomers are

A

not mirror images, chiral

57
Q

Number of stereoisomer (formula)

A

2^(n)

58
Q

Arrange from highest to least priority

A. -F
B. -OH
C. NH2
D. CH3

A

ABCD

59
Q

Arrange from highest to least priority

A. -Cl
B. -SH
C. -OH
D. -CH3

A

ABCD

60
Q

State at room temp of covalent bond and ionic bond

A

Covalent bond - gaseous or liquid

Ionic bond - solid

Organic chemistry (4 decks)

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