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Chem 51A: Midterm > Chapter 3: Organic Molecules & Functional Groups > Flashcards

Chapter 3: Organic Molecules & Functional Groups Flashcards

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1
Q

What are Heteroatoms?

A

Atoms other than carbon or hydrogen

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2
Q

What is a functional group?

A

An atom or group of atoms with characteristic chemical and physical properties. It is the reactive part of the molecule

  • something other than C-C and C-H
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3
Q

Heteroatoms have _____ _______ and create electron-deficient sits on _______.

A

Lone pairs, carbon

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4
Q

Pi bonds are easily broken in chemical reactions. A pi bond makes a molecule a _____ and a __________.

A

Base, nucleophile

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5
Q

Electrophiles are electron ________. This is because they are electron ________.

A

Loving, deficient

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6
Q

What are the 3 types of functional groups?

A
  1. Hydrocarbons
  2. Compounds containing C-Z (Z = electronegative atom)
  3. Compounds containing a C=O
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7
Q

What are the 4 types of hydrocarbons?

A

Alkanes
Alkenes
Alkynes
Aromatic compounds

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8
Q

What is the general structure for an Alkane?

A

Only have C-C sigma bonds
No functional groups

Eg, Ethane CH3CH3

R-H

(R is a carbon structure)

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9
Q

What is the general structure for an Alkene?

A

Have a C=C double bond as a functional group

Eg, Ethylene CH2=CH2

H        H
    \    /
      C
    /    \
H        H
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10
Q

What is the general structure for an Alkyne?

A

Have a C≡C triple bond as a functional group

Eg, Acetylene HC≡CH

H-C≡C-H

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11
Q

What is the general structure for an Aromatic compound?

A

These are carbon rings (or phenyl groups)

Eg, Benzene

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12
Q

List the 4 types of carbons in alkanes

A

Primary carbon 1°
- C bonded to one C

|  - C - C
|

Secondary carbon 2°
- C bonded to two Cs

C
 |  -  C - C
 |

Tertiary carbon 3°
- C bonded to three Cs

    C
     |  C -  C - C
     |

Quaternary carbon 4°
- C bonded to four Cs

        C
         |
 C -  C - C
         |
        C
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13
Q

What are the 6 types of functional groups containing C-Z sigma bonds?

(Z = electronegative atom)

A 
Alkyl Halide (Halo group)
Alcohol (Hydroxl group) 
Ether (Alkoxy group)
Amine (Amino group)
Thiol (Mercapto group)
Sulfide (Alkylthio group)
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14
Q

What is the general structure for an Alkyl halide (halo group)?

A

R-X

R = carbon skeleton 
X = F, Cl, Br, or I

Just an electronegative atom attached to a carbon skeleton!

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15
Q

What is the general structure for an Alcohol (hydroxyl group)?

A

R-OH
R-O-H

Eg,
:O:
/ \
CH3 H

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16
Q

What is the general structure for an Ether (alkoxy group)?

A

R - O - R
-OR

Eg,
:O:
/ \
CH3 CH3

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17
Q

What is the general structure for an Amine (amino group)?

A

R - NH2
R2 - NH
R3 - N

Eg,
           ..
    R - N
        /    \
      H     H
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18
Q

What is the general structure for a Thiol (mercapto group)?

A

..
R - SH
..

R - SH

Eg,
:S:
/ \
CH3 H

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19
Q

What is the general structure of a Sulfide (alkylthio group)?

A

..
R - S - R
..

R - SR

Eg,
:S:
/ \
CH3 CH3

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20
Q

What are the 6 types of functional groups containing C=O group?

A 
Aldehyde 
Ketone (carbonyl group) 
Carboxylix acid (carboxy group)
Ester 
Amide 
Acid chloride
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21
Q

What is the general structure of an Aldehyde?

A 
COH
(H attached to C=O)
         :O:
          ||
          C
        /   \
      R     H
Eg, 
         :O:
          ||
         /  \
              H
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22
Q

What is the general structure of a Ketone (carbonyl group)?

A

C=O
(C=O surrounded by R groups)

     :O:
      ||
     /  \
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23
Q

What is the general structure for a Carboxylic Acid (carboxy group)?

A 
COOH
(OH attached to C=O)
         :O:
          ||
         /  \..
             OH
             ..
24
Q

What is the general structure for an Ester?

A 
COOR
CO2R (O attached to C=O) 
         :O:
          ||
         /  \../
             O 
             ..
25
Q

What is the general structure for an Amide?

A

CONH2
Or
CONR2 (basically NH2 next to a C=O)

         :O:
          ||    H
         /  \  /
      R    :N
              |
             H
26
Q

What is the structure for an Acid Chloride?

A

COCl (Cl attached to a C=O)

     :O:
      ||
     /  \ ..
         :Cl:
27
Q

What do primary 1°, secondary 2°, and tertiary 3° amines look like?

A

Primary
C - N -
|

Secondary
C - N -
|
C

Tertiary
C - N - C
|
C

28
Q

What are intermolecular forces?

A

Interactions that exist between the molecules

29
Q

Which compounds have stronger intermolecular forces, ionic compounds or covalent compounds?

A

Ionic

30
Q

Ionic compounds are held together by extremely strong _______ ________.

A

Electrostatic interactions

31
Q

What are the 3 types of intermolecular forces for covalent compounds? List them from weakest to strongest

A

Strongest

Hydrogen bonding
Dipole-dipole interactions
Van der Waals forces

Weakest

32
Q

What are Van der Waals forces?

A

They are very weak interactions caused by the momentary changes in electron density in a molecule

Nonpolar compounds can only have van der waals

CH4 is nonpolar, but at any incident it’s electron density may not be completely symmetrical, which creates a temporary dipole. The weak interaction between two temporary dipoles in CH4 molecules creates a Van der Waals forces.

33
Q

What are two factors that affect the strength of Van der Waals interactions?

A
  1. Surface area of a molecule
    • the larger the surface area, the stronger the Van der Waals
  2. Polarizability
    • larger atoms are more polarizabke than smaller atoms, and are stronger
34
Q

What are Dipole-dipole interactions?

A

The attractive forces between the permanent dipoles of two polar molecules

Eg, in HCl molecules, they are lined up with the partial negative and partial positive charges next to each other

H-Cl - H-Cl

Cl has a partial negative charge
H has a partial positive charge
So there is a dipole-dipole interaction between the two

35
Q

What is hydrogen bonding?

A

When a H bonded to an O, N or F is attracted to a lone pair of electrons on another O, N or F

Eg, H2O

A hydrogen in one H2O molecule will have a hydrogen bond with the lone pair on the oxygen in a second H2O molecule

36
Q

What is boiling point?

A

The boiling point of a compound is the temperature at which a liquid is converted to a gas

37
Q

The stronger the intermolecular force, the ________ the boiling point.

A

Higher

38
Q

The larger the surface area, the ______ the boiling point.

A

Higher

39
Q

The more polarizable the atoms, the ________ the boiling point.

A

Higher

40
Q

In which way does polarizability increase on the periodic table?

A
41
Q

The stronger the intermolecular forces, the ________ the melting point.

A

Higher

42
Q

The more symmetrical the compound, the ________ the melting point.

A

Higher

43
Q

Polar compounds dissolve in ______ solvents.

A

Polar

44
Q

Nonpolar or weakly polar compounds dissolve in _________ solvents.

A

Nonpolar

45
Q

True or false

Many organic solvents are polar

A

False

Many organic solvents are either nonpolar or weakly polar

46
Q

True or false

Most ionic compounds are soluble in water, but insoluble in organic solvents.

A

True, because ionic compounds are held together by strong electrostatic forces

47
Q

Under what circumstances is an organic compound soluble in water?

A

If it contains one functional group

Has < 5 carbon atoms

Contains an O or N

48
Q

Explain why butane (C4H10) is insoluble in water, but acetone (C3H6O) is soluble in water.

A

Butane is nonpolar and has no functional groups, so it is insoluble in water.

Acetone has the functional group Ketone (double bonded oxygen) and it only contains 3 carbons, so its Oxygen atom can hydrogen bond with a H from water.

49
Q

If there are more than 5 carbons and only one functional group in a molecule, is the molecule soluble or insoluble in water?

A

Insoluble

50
Q

a) Which of the following can hydrogen bond to another molecule like itself?
b) Which of the following molecules can hydrogen bond with water?

       :O:
1) \ /   \ /       2) / \ .. / \
                              N
                               |
                              H
A

a) both compounds are polar, however, #1 doesn’t have a H bonded to its O, so it cannot hydrogen bond to another molecule like itself. But #2 has a H bonded to its N, so it can bond to a molecule like itself.
b) both compounds have electronegative atoms O and N, so they can hydrogen bond with a H atom in water.

51
Q

What are the two components of soap?

A
  1. A hydrophilic end composed of ions called the Polar Head.
  2. A hydrophobic carbon chain of nonpolar C-C and C-H bonds, called the Nonpolar Tail
           O
       ||
      / \   / \   / \   / \ Na+ -O     \/    \/    \/    \

^Polar ^Nonpolar
head tail

52
Q

What is a micelle?

A

A spherical droplet formed when soap is mixed with water

The hydrophilic heads point outwards and the hydrophobic tails point inwards

53
Q

How are the polar heads of a soap micelle solvated in water?

A

They are solvated by ion-dipole interactions with water molecules

54
Q

How does soap dissolve grease and oil?

A

Grease and dirt molecules are attracted to the nonpolar tails inside the soap micelle, and the hydrocarbon tails dissolve the dirt.

The polar head remains on the surface and interacts with water

55
Q

To Hydrogen bond to another molecule of itself, the molecule must contain _________________.

A

A H bonded to O, N, or F.

56
Q

To Hydrogen bond to water, a molecule needs to ____________.

A

Contain O, N, or F.

Chem 51A: Midterm (4 decks)

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