9/30 chem test

alcohols, phenols, and ethers all contain C, meaning they are all __

organic molecules

a benzene ring has

3 alternating double bonds

Hydroxy group

an OH functional group

alcohol

compound with OH group attached to R group (not a benzene ring)

“ alc OH hol “

phenol

OH attached to benzene ring (circle inside shape)

“ phen OH ring “

ether

compound with formula R-O-R

“ ether C -O -C “

naming alcohols

ordename longest chain which -OH is attached to

replace -e eith -ol

number chain so lowest gets to -OH carbon

number -Oh position and any other groups

order alphabetically

name CH3CH2CH2CH(OH)CH2CH3 (6 C’s)

3- hexanol

OH on 3rd C, 6 C’s total (hex)

name CH3CH2CH(CH3)CH(OH)CH(CH3)CH3

2,4-dimethyl-3-hexanol

2 methyls, one on the 2 and one on the 4, OH on the 3, main chain 6

naming phenols

just name group placement mostly

phenol shape with just one -OH attachment name

phenol

phenol shape with one -OH attachment, and on opposite side, -Br name

4 - bromophenol

name a phenol with 3 bromines, on the 2, 4 and 6

2,4,6-tribromophenol

which alcohols are ion chains and are therefore not very water miscible, needing nonpolar solvents

benzene and ether

BP of alcohols are ____ than alkanes and ethers, and why?

higher, due to H bonding

What temperature means dehydration producing alkene reaction

180

CH3CH(OH)CH3 —→ react acid / 180

CH3C (H) = CH2 + H2O

dehydrations create double bonds and turn alkane into alkene

O moved from OH to H2O, H on second C moved to H2O, replaced by double bond

dehydration ether producing ether temperature

140

CH3CH2OH + HOCH2CH3 —→ ACID / 140

CH3CH2OCH2 + H20

H from OH and from HO move to H20, so does O of OH

Oxidation reaction

(o) symbol, molecule gains O atom or loses H atom

primary alcohols oxidize to what, secondary and tertiary?

primary aldehyde (O=C-H-R), secondary keytone (O=C-R-R) tertiary no reaction, in start no H on C so can’t oxidize

dehydration synthesis always forms partly

H2O

alkene, alkyne, alkane

kane single bond, kene double, kyne triple

a cyclo pent alkene becomes cyclo pent with no inside double bonds and one outside double bond to o; what caused this and what step was inbetween

H20 / ACID —→ cyclo with no double bonds and an OH group, —> (o) turns it into end result

phenol traits (melt point and behavior in h2o)

low melt point, weak acid in water

naming ethers

name the smaller of the two R groups as an alkoxy group attached to the parent chain by replacing the -yl ending of the R group with -oxy

name CH3CH2-O-CH2CH2CH3

1-ethoxypropane

use propyl (longest group) as parent chain, o is dividing sections. O is attached to first C of longest C chain

CH3-O- phenol (?) ring name (ring with circle in middle)

methoxybenzene

heterocyclic ring

ring that contains atoms other than C

ether properties (polarity, solubility, boil and melt points, reactivity and flammability

less polar than alcohols, more soluble than hydrocarbons but less than alcohols, low BP and MP, (because of inability to form H bonds with other ethers), unreactive, highly flammable

Thiol

compounds that contain the -SH group (sulfhydryl functional group)

name CH3CH2SH

ethanethiol

thiol reactions / coupling reaction

when thiols undergo oxidation, they form disulfide linkage (R-S-S-R), so a thiol becomes a disulfide

CH3SH + CH3SH [o] —→

CH3-S-S-CH3

thiol reduction

oxidation can be reversed with a reducing agent H2 for example

CH3SH + CH3SH —→ Hg²+

CH3-S-HG-S-CH3

thiol bonds w mercury need more help on this

polyfunctional compounds have

2 or more functional groups, which are what determine chemical properties of compounds

cholesterol

should exhibit the reactions of both alkenes and alcohols

carbonyl group

C with = to O

aldehydes

at least one H atom attached to caybonyl

ketone

2 carbons attached to carbonyl

ending of aldehyde / ending of ketone

-anal and -one

naming aldehydes

longest chain, replace e with -al; carbonyl C will always be at end, it is designated carbon 1

name CH3CH3(BR)CH2C=O (on top, then continue) -H

3-bromobutanal

-al ending, bromo group is at the 3 because the C with = o will always be 1

naming ketones

normal rules -one end, chain is numbered from the end closest to the carbonyl group

name CH3C=O CH (CH3) CH2CH3

3-methyl-2-pentanone

u get it

ketone + aldehydes boiling point

lower than alcohol, because they can’t form H bonds; higher than alkanes because of dipole dipole interactions (not symmetrical)

why are ketones and aldehydes with low MW soluble in H2O

carbonyl oxygen has dipole dipole and forms H bonds

2 things oxidation reaction can do

add O bond, break H bond

oxidation: tollens reagent

mild oxidizing agent with Ag, metallic; ketones wont react with it

oxidation: benedict’s test

mild oxidizing solution with Cu 2+, make red color

addition of hydrogen in chemical reactions

catalyst pt or pd

hemiacetals vs acetals

form when aldehydes and alcohols react

hemi have OH and O-R group, unstable; ace have 2 O - R groups instead, stable

hemiketals vs ketals

both form when alcohols react with ketones, hemi have 3 C with an OH and O-R on one, ket have 3 C with 2 O-R on one

hydrolysis

bond breakdown by reaction with water, acetals and ketals break back down into aldehydes and ketones +additional alcohol

hemiace + hemiket can be cyclic. in H+ (hydrolysis) reaction, what changes

things that are attached to the C with the R groups, only H2O remains separate