all of ochem 2 lol kms

what are carbs bro (three points)

• polyhydroxy aldehydes or ketones

• remain sugars even if the hydroxy
  groups can be removed (deoxy sugars)

• or replaced by amine (amino sugars)

monosaccharide

saccharides, the simplest form of carbohydrates, consisting of single sugar units.

oligosaccharide

a carbohydrate composed of 2 to 10 monosaccharide units linked together by glycosidic bonds.

polysaccharide

long chains of monosaccharide units linked by glycosidic bonds (more than 10), serving as energy storage or structural components.

Mutarotation

is the change in optical rotation that occurs when an alpha or beta anomer of a sugar interconverts in solution, resulting in a mixture of both forms.

aldotetroses

erythrose and threose

aldopentoses

ribose, arabinose (2), xylose (3), lyxose (2,3)

aldohexose

allose, altrose (2), glucose (3), mannose (2,3), gulose (4), idose (2,4), galactose (3,4), talose (2,3,4)

anomer

A type of stereoisomer that differs in configuration at the anomeric carbon, typically found in carbohydrate chemistry.

acid chloride/symmetric acid anhydride, pyridine

all oh groups react

CH3I, Ag2O

all oh groups react

ROH, HCl

turns hemiacetal to acetal OR replaces anomeric OH with OR

1. HBr

2. ROH, Ag2O

3. NaOH, H2O

koenigs-knorr reaction mechanism (c1 glycoside formation only)

NaBH4, H2O

reduction

1. Br2, H2O

2. ph = 6

oxidation

HNO3, H2O, heat

dicarboxylic acids (both top and bottom as oxidized)

HCN, H2, H3O

kiliani-fischer synthesis, adds a C

NH2OH, (CH3CO)2O, NaOCH3

wohl degradation, takes off a C

cellulose

monomer: glucose (pyranose form)

linkage: beta 1→4 bonds

function: structure

amylose

monomer: glucose (pyranose form)

linkage: alpha 1→4 glycoside bonds

function: energy storage

amylopectin

monomer: glucose (pyranose form)

linkage: alpha 1→4 and alpha 1→6 glycoside bonds

branching: yes

function: energy storage

glycogen

monomer: glucose (pyranose form)

linkage: alpha 1→4 and alpha 1→6 glycoside bonds
branching: yes

function: energy storage in animals

enolate

a negatively charged carbon-containing compound formed by removing a proton from the alpha-carbon

enol

an organic compound characterized by a carbon-carbon double bond (alkene) with a hydroxyl group (-OH) directly attached to one of the double bond's carbon atoms

X2, acetic acid (CH3COOH)

1. Br2, PBr3

2. H2O

hell-volhard-zelinskii rxn, to brominate carboxylic acids

Relative acidity of carbonyl groups

o Carboxylic acids (MOST acidic, pKa ~5)
o diketones
o ketoesters
o diesters
o Alcohols (pKa ~16)
o Aldehydes
o Ketones
o Thioesters
o Esters (LEAST acidic)
o Nitriles
o Amides

X2, NaOH

methyl ketone that turns to COOH

H3O, heat

boots a COOH off

NaOet, EtOH

booted an H from an alpha carbon and replaces

LDA, THF → RX

boots an alpha-hydrogen for ketones, esters, and nitriles

mass spec indicates

molar mass, elements present, molecular formula, cation fragments

base peak

peak w 100% relative abundance

parent peak

aka M+ peak, the peak corresponding to the molecular ion of the compound, representing the intact molecule.

odd MW

indicates N

3:1 M & M+2

indicates Cl

1:1 M & M+2

indicates Br

branched alkane fragmentation pattern

breaks @ branch points

alcohol fragmentation pattern

alpha carbon fragmentation or dehydration (lose water, M minus 18)

amines fragmentation pattern

alpha cleavage

carbonyls fragmentation pattern

alpha cleavage and mclafferty (alpha and beta carbon bond breaks, OH forms)

finding degree of unsaturation

[(2C + 2) + N - H - X] / 2

finding number of carbons

[(M + 1)/M+] / 1.1

what is UV-vis

conjugated molecules absorb in UV region, excitation of electrons in molecular orbitals

what does IR show

presence of a functional group, bonds stretching/bending

fingerprint region on IR

400-1500

double bonds on IR

1500-2000

triple bonds on IR

2000-2500

NH, CH, and OH in IR

2500-4000

C-C-H on IR

just below 3000

C = C - H on IR

just above 3000

C =- C - H on IR

more above 3000

C - C on IR

800-1300

C = C on IR

1640-1680

C =- C on IR

2100-2260

benzene fingers

A region in the IR spectrum, typically around 1450-1600 cm^-1, associated with C=C stretching and other bending vibrations in aromatic compounds.

OH on IR

3400-3650

amine (R-N-H2) on IR

3300-3500

C=O on a saturated aldehyde on IR

1730

C=O from an aldehyde next to an aryl or double bond on IR

1705

ketones on a 6 atom ring on IR

1715

ketones on a 5 atom ring on IR

1750

ketones next to a double bond/aryl ring on IR

1690

esters on IR

1735

esters by a double bond on IR

1715

what does NMR show

number of unique C or H, func groups + connections, structure

shielding

opposing magnetic field produced by electrons surrounding nuclei to counteract external magnetic field

looking at an NMR chart

left = downfield, deshielded

right = upfield, shielded

C13 NMR vs DEPT90 vs DEPT135

shows all vs shows only CH vs CH and CH3 are positive, while CH2 is negative

enantiotopic vs diastereopic

Enantiotopic refers to groups that are related as mirror images, while diastereotopic refers to groups that are not related by such symmetry. These terms help distinguish between different types of stereoisomers.

area under an NMR peak

proportional to the # of protons → integration = relative # of protons whereas splitting shows # of adjacent protons

more conjugation

more stable, less energy, HOMO to LUMO jump is less, max wavelength increases, colors appear (400-800 nm)

lone pair on N in 6 membered ring

isn’t counted for aromaticity

lone pair on N in 5 membered ring

one pair can count for aromaticity

toluene

xylene

indene

naphthalene

biphenyl

anthracene

phenanthrene

aniline

nitrobenzene

phenyl vs benzyl group

carbocation rearrangement for alkylation

benzene will stick itself to the more substituted group

flaws w/ alkylation

polyalkylation, carbocation rearrangements, can’t happen with strongly deactivating groups

friedel crafts alkylation vs acylation

Br2 / FeBr3

SO3 / H2SO4 and HNO3 / H2SO4

F-TEDA-BF4

I2 / CuCl2

Fe, H3O+ / HO-

NBS

H2 / PDC

reduces alpha carbon double bond to single bond or NO2 to NH2

EAS vs NAS mechanism

formaldehyde

acetaldehyde

benzaldehyde

acetone

acetophenone