chem 108 midterm 3

ch 10-13

Alkanes

Alkene

Alkynes

aromatic ring

Alcohol

Amine

Aldehyde

Ketone

Carboxylic Acid

Ester

Ether

benzene

Phenol

Amide

thiol

carbonyl

Thioester

meth-

1 group

eth-

2 groups

hept-

7 groups

oct-

8 groups

non-

9 groups

Carboxylic Acid

naming alkenes + alkynes

1. find longest chain (parent chain) that includes double/triple bond *make sure to count carbons on both sides! LOWEST NUMBER!)

2. name branches and list by alphabetical order

3. indicate which carbon starts the double/triple bond

4. end w/ parent root + -ene OR -yne

   FOR AKLENES ONLY: MAKE SURE TO INDICATE IF STRUCTURE IS CIS OR TRANS

   (example would be trans-4,4-dimethyl-2-heptene)

naming cycloaklanes with branches

1. count the carbons in the ring (lowest number to branches)

2. list branches in alphabetical order

3. branches + cyclo-parent name-ane

   (example would be 1-ethyl-3-methylcyclopentane)

meth-

1 group

oct-

8 groups

naming phenols

1. the carbon attached to the OH will always be the first carbon!

2. lowest numbers for branches

3. branches + phenol

   (example would be 2-ethyl-3-methylphenol)

naming amines

1. name branching groups add prefixes if needed

2. alphabetize!

3. end with -amine

   (example would be dimethylamine)

naming aldehydes

1. carbon attached to aldehyde group will be the first carbon!!

2. name branches and alphabetize them

3. branches + root-anal

   (example would be 4-methylpentanal)

naming ketones

1. find longest carbon chain, lowest number for carbon double bonded to oxygen

2. branches + root-anone

   (example would be 1,2-dimethylbutanone)

naming carboxylic acids

5 groups

hex-

6 groups

hept-

7 groups

Ester

Ether

naming alcohols + thiols

1. number parent chain w/ the lowest number for OH/SH

2. name branches and number where the OH/SH is

3. branches + root-anol OR branches + root-thiol

   (example is 5-methyl-3-hexanol)

dec-

10 groups

naming alkanes

1. find longest chain (parent chain) w/ lowest number to first branch

2. name branches

3. list branches by alphabetical order

4. end w/ parent root + -ane

   (example would be 3-methyl-pentane)

naming alkenes + alkynes

carboxylic acid

naming cycloaklanes with branches

1. count the carbons in the ring (lowest number to branches)

2. list branches in alphabetical order

3. branches + cyclo-parent name-ane

   (example would be 1-ethyl-3-methylcyclopentane)

naming aromatic rings

ketone

true or false: tertiary alcohols can be oxidized

false

reduction of aldehydes and ketones

1. draw hydrogen on adjacent carbon

2. add hydrogen to both oxygen and carbon

aldehydes/ketones + H/NADH (red) =

alcohol

catalytic hydrogenation

3 groups

but-

4 groups

pent-

5 groups

hex-

6 groups

hept-

7 groups

oct-

8 groups

h+ is also known as…

a catalyst

ester + h20

carboxylic acid + alcohol

naming aldehydes

1. carbon attached to aldehyde group will be the first carbon!!

2. name branches and alphabetize them

3. branches + root-anal

   (example would be 4-methylpentanal)

naming ketones

1. find longest carbon chain, lowest number for carbon double bonded to oxygen

2. branches + root-anone

   (example would be 1,2-dimethylbutanone)

naming carboxylic acids

1. carbon attached to aldehyde group will be the first carbon!!

2. name branches and alphabetize them

3. branches + root-anoic acid

   put space in between root-anoic and acid!

oxidation of alcohols

1. draw hydrogens in adjacent carbon

2. first oxidation: remove hydrogen from carbon and oxygen

3. second oxidation: add OH to carbon

secondary alcohols + [O]/NAD+ (ox) =

ketone

benzene

oct-

8 groups

amide + h20

carboxylate + ammonium atom (NH3+ and R)

alcohol + cat/H+/heat/delta

alkene + h2o

-for more substituted carbons, remove H from them

alkene + h2o/catalyst/h+

alcohol

structural isomers

same formula, different connectivity

-must have at least 4 carbons

-have different physical properties

increase intermolecular forces?

increase melting and boiling point

intermolecular forces and surface area

more branches DECREASE surface area which will DECREASE boiling point

geometric isomers

same formula, same connectivity, different 3D shape (alkenes)

cis

hydrogens are on the same side of double bond

naming esters

1. regions are separated between two oxygens!

2. name branch bonded to oxygen

3. number carbon chain doubled bonded to other oxygen

4. branch bonded to oxygen (space) branches + root-anoate

naming amides

1. count carbons in parent chain w C=O bond and name branches

2. name branches bonded to nitrogen

3. alphabetize!

4. branches + root-anamide

oxidation

increase in oxygen, decrease in hydrogen

the more carbon groups…

the more nonpolar the chemical is

hci

add hydrogen to reactant + cl-

acid + base

base gains a hydrogen and a positive charge + naked acid (no hydrogen) w/ negative charge

[O]/NAD+

oxidize

[H]/NADH

reduce

H2/metal/[H]

only alkenes! catalytic hydrogenation or reduction

H+/Cat/heat/delta

dehydration

H2O/H+/Cat (alkene)

hydration

H2O/Cat

hydrolysis