Ochem Final

Front 1

What is a common feature of Carboxylic acids and derivatives?

Back 1

They contain an acyl group bonded to an electrongeative atom or substituent, that can act as a LG.

Front 2

Three rules of naming carboxylic acids (RCO2H)?

Back 2

1. Replace -e w/ -oic acid
2. -CO2H carbon is # C1
3. Bonded to a ring (-CO2H) use carboxylic acid. ie cyclopent-1-ene carboxylic acid.

Front 3

Name these acids
HCO2H
CH3CO2H

Back 3

Formic acid
Acetic acid

Front 4

Most carboxylic acids exists as _____ held together by 2 _____ bonds.

Back 4

dimer
hydrogen

Front 5

T or F
Esters have a plesant smell and are present in animal fats?

Back 5

True

Front 6

What is the formula for an Ester?

Back 6

CH3CO2R

Front 7

T or F
Amids are least reactive of the common acid derivative and are thus stable.

Back 7

True

Front 8

What is the formula for Amids?

Back 8

NH2 is attached at some point.

Front 9

Are acid Chlorides and anhydrides found in nature?

Back 9

No

Front 10

Why are acid Chlorides and anhydrides not found in nature?

Back 10

They are highly reactive.

Front 11

What is the acidity of Carboxylic Acid? pKa =

Back 11

pKa = 4.76
Ka = 1.75x10^-5

Front 12

When Carboxylic acid react with NaOH, you get?

Back 12

a water soluble metal carboxylates RCO2- Na+

Front 13

Is Carboxylic Acid a stronger acid than alcohols and phenols?

Back 13

Yes.

Front 14

Why is Carboxylic Acid a stronger acid then alcohols and phenols?

Back 14

because the charge is spread across both O atoms due to resonance.

Front 15

T or F
The more stabilized the carboxylate anion, the stronger the acid.

Back 15

True.

Front 16

the synthesis of Carboxylic Acid oxidation is done using what two chemicals? and what does each add?

Back 16

done with KMnO4
adds 2 O's
done with (the molecule has a C=O bond already) CrO3 and adds 1 O.

Front 17

Nucleophilic Acyl Substitution Rxn.
Aldehyde or Ketone Nu: addition...explain the details

Back 17

Nu: attaches to C and double bond breaks. O has a (-) change now. H3O+ is added and the O takes an H creating an alcohol.

Front 18

Nucleophilic Acyl Substitution Rxn.
Carboxylic Acid derivative Nu: substitution

Back 18

Nu: attaches to C double bond breaks. O has a (-) charge now. the O e- go back onto the bond creating a double bond again and knocking off the LG.

Front 19

In a Nucleophilic Acyl Substitution Rxn., which step is the rate limiting one?

Back 19

the addition step.

Front 20

What does Acyl mean?

Back 20

RCO-

Front 21

An Aldehyde or Ketone Nu: addition ends in what CO bond?

Back 21

single bond

Front 22

An Carboxylic Acid Nu: substitution ends in what CO bond?

Back 22

double bond

Front 23

List the 5 common carboxylic acids from least reactive to most reactive.

Back 23

Amid
Ester
Thioester
Acid Anhydride
Acid Cloride

Front 24

Hydorlysis is a rxn with ____ and yeilds ______.

Back 24

H2O
Carboxylic Acid

Front 25

Alcoholysis is a rxn with _____ and yields ______.

Back 25

-OH
Ester RC=OOR

Front 26

Aminolysis is a rxn with _______ or an ______ and yields _____.

Back 26

ammonia or amine
Amide

Front 27

Reductions is a rxn with ____ to yield _____.

Back 27

Hydride (hydrogen being nucleophilic ie. :H-) reducing agnet
-OH or alcohol

Front 28

Grignard is a rxn with _____ to yield _______

Back 28

RMgX
-OH

Front 29

Carboxylic Acids and Their rxns
Substitution is done using 2 methods.
1.
2.

Back 29

1. using strong acid to protonate (H3O) to give an -OH
2. convert -OH into a better LG.

Front 30

Carboxylic Acids and Their rxns
to convert a Carboxylic Acid into an acid chloride you use what chemical?

Back 30

SOCl2

Front 31

Carboxylic Acids and Their rxns
to convert a Carboxylic Acid into an Ester you use what?

Back 31

Fisher esterification rxn.
The OH is removed and the CH3CH2OH is added. RC=OOCH2CH3 + H2O

Front 32

Carboxylic Acids and Their rxns
Ester is formed when using an ______solvent.
Carboxylic acid is formed when using an ______ solvent.

Back 32

-OH
H2O

Front 33

Most of the chemistry of carbonyl compounds can be explained by 4 fundamental reactions. What are the first 2?

Back 33

1. The nucleophilic addition reaction of Aldehydes and Ketones
2. the nucleophilic acyl substitution reaction of carboxylic acid derivatives.

Front 34

Review Exam 1:
Name each type of bond:
1. Equal sharing of electrons
2. Unequal sharing of electrons
3. no sharing of electrons at all

Back 34

1. Non polar covalent bond
2. polar covalent bond
3. Ionic Bond

Front 35

Review Exam 1:
Pi bonds are made from the overlap of?

Back 35

the p orbital (at both ends)
They are sideways overlaped

Front 36

Review Exam 1:
Sigma bonds are made up of the overlap of?

Back 36

the sp3-sp3 hybrid bond
They are end on end overlaped

Front 37

Review Exam 1:
What is a lewis Acid and lewis Base

Back 37

Lewis acid it an electron acceptor, lewis base is an electron donor.

Front 38

An sp2 hybrid has what type of bond and what type of shape?

Back 38

Double bond
Trigonal planar shape.

Front 39

Review Exam 1:
sp1 has how many equivalent sp orbitals and how many unhypridized

Back 39

2,2

Front 40

Review Exam 1:
sp2 has how many equivalent sp orbitals and how many unhypridized

Back 40

3,1

Front 41

Review Exam 1:
sp3 has how many equivalent sp orbitals and how many unhypridized

Back 41

4,0

Front 42

Review Exam 1:
state the Hand's Rule

Back 42

when empty orbitals of equal energy are available 1e- occupies each w/ parallel spins.

Front 43

Review Exam 1:
State Avfbau principal

Back 43

Start at the bottom and build your way up.

Front 44

Review Exam 1:
State the polyexclusion principal

Back 44

only 2e- w/ different spin can be in an orbital.

Front 45

Review Exam 1:
In Newman projections the staggard configuration is higher in energy. T or F

Back 45

False

Front 46

Review Exam 1:
In Newman projections the eclipsed configuration is higher in energy. T or F

Back 46

True, because the "clouds" are bumping.

Front 47

Review Exam 1:
In Newman projections which is more stable. Eclipsed or Staggered?

Back 47

Staggered is more stable.

Front 48

Review Exam 1:
What are steroisomers?

Back 48

Have the same formula and structure, but different in space due to bond rotation

Front 49

Review Exam 1:
What are constitutional isomers?

Back 49

Have the same formula, but different connections.

Front 50

Review Exam 1:
What is a cis isomer and a trans isomer?

Back 50

Cis = same side of the molecule
Trans = opposite side of the molecule.

Front 51

Review Exam 1:
List what each scientist discovered.
Kekule
Watson & Crick
Pauling
Wohler

Back 51

Chemical structure
DNA structure
Electronegativity
Organic cmpd formed from inorganic cmpds.

Front 52

Review Exam 1:
Saturated hydrocarbons have _____ hydrogens attached to the carbons

Back 52

the max number

Front 53

Review Exam 1:
What is a conformational isomer?

Back 53

The isomer can be interconverted due to the rotation of the C-C bond.

Front 54

The chair conformation of cyclohexane contain what type of strain.

Back 54

no strain

Front 55

Review Exam 1:
Angle strain you should think of?
Steric strain you should think of?

Back 55

A cyclopropane
An Ethyl (Newman projection)

Front 56

Review Exam 1:
In the chair conformation the axial bonds are?

Back 56

up and down/parallel

Front 57

Review Exam 1:
in the chair conformation the equitorial conformation bonds are?

Back 57

parallel to one bond over.

Front 58

Review Exam 1:
In the chair conformation the more stable conformation will have the largest molecule in the _____ bond

Back 58

equitorial

Front 59

Review Exam 1:
When prediction which side a reaction will favor the reaction runs to the side with the weak acid and weak base. T or F

Back 59

True