OChem

Question 1

Thin Layer Chromatagraphy

Answer 1

• Non-polar travels faster (the chamber is polar-sillica)

Question 2

IR with numbers

Answer 2

OH 3200-3500
C=O 1700
C-H 3000-3300

Question 3

number of signals=# of types of protons in the environment

Answer 3

Question 4

H NMR chemical shift

Answer 4

-an electronegative substituent withdraws electrons–>deshields neighboring protons from the magnetic field–>downfield/larger chemical shift–>leftward

Question 5

Mass spectrometry

Answer 5

how it works

Question 6

Interpreting IR spectra

Answer 6

Question 7

Dipole-dipole force

Answer 7

-uneven distribution of electrons
-must in polar molecules eg: H2O-bent & electronegative

Question 8

carbocation stability

Answer 8

carbanions-the opposite
more stable=less reactive=lower energy

Question 9

Stabilization of organic intermediates

Answer 9

-inductive effects-via sigma bonds
-resonance effects-via pi bonds

Cl very electronegative–>making the ions more stable through inductive effect

Question 10

sigma and pi bonds

Answer 10

Question 11

inductive effect-having an electron negative atom pulling electron density away

Answer 11

F makes the conjugate base less negative–>weak base–>stronger acid–>lower pka

Question 12

How to rank acidity

Answer 12

the more stable the conjugate base, the stronger the acid is

Question 13

Strength of intermolecular forces

Answer 13

Question 14

primary substrate–>SN2

Answer 14

“one person pushing another off a swing” (backside attack, one step).

Question 15

Tertiary substrate–> SN1

Answer 15

a unimolecular mechanism, i.e. only one of the reactants (in this case the substrate) participates in the rate-determining

Question 16

Secondary substrates?

Answer 16

-Strong nucleophile does SN2, weak nucleophile does SN1
-strong nucleophile–>highly reactive/unstable–>has a large electron density (unhappy)–>not going to wait for the leaving group to leave before it attacks

Question 17

Common strong nucelophiles

Answer 17

Question 18

two types of solvents

Answer 18

-polar aprotic solvents favor the SN2 mechanism–>allow nucelophiles to move around freely and be more reactive
-polar protic solvents favor the SN1 mechanism–>they effectively stabilize the carbocation intermediate formed during the reaction through hydrogen bonding

Question 19

stereochemistry of the product

Answer 19

• SN2 mechanism goes through inversion of configuration
• SN1 mechanism goes through the racemization

Question 20

Structual isomers=constitutional

Answer 20

same chemical formula, different bond arrangement

Question 21

diastereomers

Answer 21

• differ at some, not all chiral centers

Question 22

conformational isomers

Answer 22

Question 23

Glycerol structure

Answer 23

Question 24

Counting isomers

Answer 24

Question 25

Aldo-condensation | https://www.youtube.com/watch?v=OBT3otCRBxg

Answer 25

* six carbon ring is the most stable * Kinetic Products: less stable--> formation of the **less substituted** β-hydroxy carbonyl compound * The Hs on alpha carbons will be deprotonated (-)-->attack the carbon on the carbonyl. * Elimination process

Question 26

SN2

Answer 26

* favors carbons with less c attached * polar aprotoic solvent

Question 27

UV Spectroscopy

Answer 27

Question 28

Mass spectrometry

Answer 28

Question 29

NMR Shielding & Deshielding

Answer 29

Downfield=leftwards

Question 30

sulfoxide

Answer 30

polar

Question 31

DMF

Answer 31

Question 32

acidity

Answer 32

conj base (negative charge) more stable-->weaker conj base-->stronger acid

Question 33

neucleophillic addition to C=O

Answer 33

Question 34

cyanohydrin

Answer 34

Question 35

keto-enol tautomerization

Answer 35

Question 36

sigma and pi bonds

Answer 36

Question 37

anhydride

Answer 37

Question 38

Enamine

Answer 38

Question 39

resonance stabilization between amides and esters

Answer 39

Question 40

lactams

Answer 40

Question 41

Methanol

Answer 41

Question 42

number of carbons

Answer 42

Question 43

Nucelphilic acyl subsititution

Answer 43

Question 44

E/Z isomers

Answer 44

Question 45

aldo condensations

Answer 45

* 1 st-aldo addition * 2nd-elimination

Question 46

oxidizing agents

Answer 46

Question 47

SOCl2

Answer 47

SOCl2 is used to create acyl halides and not carboxylic acids

Question 48

SN1 rxn

Answer 48

Question 49

estrogen & aldosterone

Answer 49

Question 50

alkoxide

Answer 50

Question 51

susbtituted aromatic

Answer 51

stronger IMF=higher BP

Question 52

Enthalpy Change (ΔHf)

Answer 52

Question 53

Relative stabilization energy (RSE)

Answer 53

* Determines how much a substituent stabilizes a carbocation intermediate. * More negative the **RSE, the greater the stabilization**

Question 54

stablizing carboncation

Answer 54

* If a substituent can **contribute some electron density** to the carbocation the species is stabilized. * Carbocations are typically **unstable** due to their **high concentration of positive charge**

Question 55

**sigmoidal curve function**

Answer 55

Question 56

opaque

Answer 56

not see through/transparent

Question 57

Amide Group

Answer 57

-C=O-NH2

Question 58

Amine

Answer 58

R-NH2

Question 59

**Diastereomers **

Answer 59

have at least one but not all chiral centers differing in configuration.

Question 60

triacylglycerol structure

Answer 60

Question 61

phospholipid structure

Answer 61

Question 62

steroid hormone structure

Answer 62

Question 63

tollen's test

Answer 63

* used to detect reducing sugars * C=O reduce Ag+

Question 64

acetal

Answer 64

Question 65

anomeric

Answer 65

Question 66

tips on calculating a.a. PH

Answer 66

* at PH=7; N terminus and C terminus cancel out * Ignore non-charged a.a.

Question 67

Thin Layer Chromatography

Answer 67

* If the molecule you want to catch is polar (like a Glutamine amino acid residue), you’ll use polar beads. * non-polar elute first

Question 68

Reverse thin Layer Chromatography

Answer 68

* Mobile Phase (Polar) Flows First * Most polar compound elutes first (prefers mobile phase). * Less polar compounds elute later (more interaction with stationary phase).

Question 69

ATP structure

Answer 69

Question 70

Cholesterol structure

Answer 70

Question 71

GTP structure

Answer 71

* GTP is more specialized, mainly involved in protein synthesis, signal transduction (GPCRs), and microtubule dynamics. * Both have similar triphosphate groups and release energy via hydrolysis.

Question 72

ether

Answer 72

Question 73

plasma proteins-albumin

Answer 73

* draws water back into the capillaries from the surrounding interstitial fluid *

Question 74

thiol group

Answer 74

* cysteine-only a.a. that has thiol group

Question 75

Chaperone proteins

Answer 75

* helpers or bodyguards inside cells that make sure other proteins fold into the right shape so they can work properly.

Question 76

tertiary structure

Answer 76

Question 77

E1 Rxn

Answer 77

* E1 is SN1’s cousin — slow start, rearranges, and Zaitsev’s favorite

Question 78

E1 Rxn mechnisim

Answer 78

Question 79

lipase

Answer 79

* break down of fats

Question 80

ribose

Answer 80

Question 81

Glycogen

Answer 81