alcohols and derivatives aldehydes and ketones

are alcohols water soluble

short chain alcohols are water soluble but long chain (>5) insoluble

study and memorize the functional groups based on their oxidation state

what is the name of the benzene that is an alcohol

phenol

what are alcohols used as

disinfectants, paint thinners, recreational purposes

why does alcohol have a hydrophobic effect (bu tam doğru bi soru mu anlamadım ama hydrophobiccen direk delta S>0 yani entropy var)

due to entropy increase (increased mobility/ disorder/ degrees of freedom)

what kind of alcohol is in hand sanitizers

ethanol

how do hand sanitizers work

at 70% ethanol the interactions between proteins and water are replaced by interactions with ethanol. these weak forces destabilize the structure of proteins, that lose their function. viral proteins constituents of the capsid destabilized, and the virus loses its infectivity

is ethanol ampiphatic

yes it’s both hydrophobic (Ch3CH2-) and hydrophilic (-OH)

what does thio- indicate

presence of sulfur

what is the substituent in thiols

-SH sulfhydryl group

why are thiols more volatile than alcohol

because sulfur is a poor hydrogen bond acceptor

what do thiols react with to form a thioester

acids

why are ethers even more volatile

because it has dipole dipole interactions

are ethers soluble in water

poorly soluble in water

what is alcohols’ reactivity due to

-the polarized c-o bond

-the presence of lonr pairs on the oxygen, making the alcohol a nucleophile

what happens if we oxidize an alkane twice

first oxidation it becomes an alcohol

second oxidation it becomes a ketone/aldehyde (primary alcohol creates aldehyde secondary alcohol creates ketone)

alcohols properties

on/off switch to signal events inside/ outside the the cell

breakdown/ synthesis intermediate metabolites

attachment points for several chemical modifications (alcohols are reversable they can turn into something and then turn back on)

what do we get when we oxidize a phenol

quinone

what to alcohols react with to form esters

acids (organic or inorganic)

what are phosphate esters’ job in biology

-in dna and rna nucleotides are linked together via phosphodiester bonds

-amino acids with -OH functions can be modified to form phosphate esters, modifying the protein structure and function

when can an alcohol be dehydrated

only if there is a hydrogen on the carbon next to the one carbon atom bearing the -OH function

are alcohols acids or bases

they are amphoteric (electron withdrawing groups make the alcohol more acid and electron donating ones make them less acid) (positively charged acidic negatively charged basic most of the time)

which one is more acidic alcohols or thiols and why?

thiols are more acidic because the S-H bond is longer and weaker than the C-H bond

sulfur is more polarizable

thiols are very good nucleophiles (since the lone pairs are less attracted by the atom thanks to lower electronegativity)

with which method are the conjugated bases stabilized

resonance (electron delocalization in molecules when there is multiple lonr pairs)

what protonates alcohols

strong acids

what is protonation

the chemical process where a molecule or ion gains a proton

what is a cystine

a covalently-linked dimer from the oxidation of two cysteine molecules

which amino acid has a thiol function

cysteine (natural component of proteins)

(under stress conditions it can be oxidized to a variety of acid forms)

what is the hybridization of the carbon atom in carbonyl groups

sp2

what is the composition of carbonyl groups

planar with 120 degree angles between the bonds

what are the carbon atoms adjacent to a carbonyl are called

carbon 2 and carbon alpha

what is a keto-enol tautomerism

when at least a hydrogen is present on the alpha carbon, aldehydes and ketones can go under a rearrangment (tautomerization) to an enol

keto and enol properties

which is more stable and favorable keto form or enol form

keto form

what is an enol

alkene molecule containing a hydroxyl group

why is the keto enol tautomerism not a resonance

because it involves the movement of atoms, specifically a proton and the relocation of electrons, resulting in two different chemical compounds with distinct features (yani sadece bondun yeri değişse resonance olur ama burda o ya h de bağlandığı için sayamayız galiba)

sunumun 16-17. sayfasındaki anlamadığım yerler var onları deganoya sormayı unutmamak için not alıuorım

wowoowowow

what are methanal - ethanal - 2-propanone (dimethyl ketone) common names

methanal = formaldehyde

ethanal = acetaldehyde

2-propanone = acetone

name all these

alr named on the photooooo

between nucleophiles and electrophiles which one is a donor and which one is an acceptor in a hydrogen bond

nucleophiles are donors (they attack) and electrophiles are acceptors

in a hydrogen bond is carbonyl an acceptor or a donor

carbonyl is an acceptor because carbonyls are electrophiles

going from alkane to aldehyde to ketone to alcohol does the boiling point increase or decrease

the boiling point increases

alkane 0 degrees

aldehyde 49 degrees

ketone 56 degrees

alcohol 97 degrees

why are pure ketones/aldehydes low boiling liquids

they have dipole dipole interactions and the carbonyl group has a strong dipole

aldehyde and acetone in water creating hydrogen bonds

can aldehydes and ketones be oxidized to the corresponding organic acids

only aldehydes can ketones can’t

what is used to distinguish ketones from aldehydes

tollens’ reagent (Ag+ ions in solution with ammonia)

what are aldehydes and ketones reduces by

H2 or NaBH4 (sodium borohydride) and catalyst such as nickel, platinum, palladium

aldehydes are reduced to primary alcohols and ketones are reduced to secondary alcohols

what do we get when an alcohol reacts with an aldehyde or ketone

hemiacetal (very unstable)

what forms when an alcohol is added to a hemiacetal

acetal (more stable than hemiacetal)

which one is more stable for hemiacetals cyclic form or open-chair form

cyclic form

formation of a cyclic hemiacetal

the formation of acetal is at the basis of which bond’s formation

this reaction is at the basis of the formation of the glycosidic bond between sugar units

cyclic hemiacetal turning into cyclic acetal

compounds with R-NH2 structure reacting with the carbonyl group

what is the product of a reaction between an ammonia and carbonyl group called

schiff bas (imine) + H2O

where is the aldol reaction most important

in the metabolism of glucose. in the breakdown of glucose we encounter a retro-aldol reaction

what is the product of an aldol reaction

3-hydroxy aldehyde (or ketone) “aldol”, “ketol”

what happens in an aldol reaction

the base shifts the equilibrium towards thr enolate form, and the carbanion can perform a nucleophilic attack on the carbonyl

glucose catabolism