chapter 12 - alcohols, aldehydes, thiols, ethers, keytones

identify the fxn group

• alcohols

• has an -OH attached (single bonds)?

example: name the following

5-methyl-3-hexanol

example: name the following

4-methyl-2-hexanol

how are alcohols classified?

with degrees

• 1 degree, 2 degrees, 3 degrees

fxn group with a -OH and single bonds

alcohol

what is a 1 degree alcohol?

1 carbon directly attached to the carbon of the -OH

what is a 2 degree alcohol?

2 carbons directly attached to the carbon of the -OH

what is a 3 degree alcohol?

3 carbons directly attached to the carbon of the -OH

another term for a 1 degree alcohol?

primary alcohol

another term for a 2 degree alcohol?

secondary alcohol

another term for a 3 degree alcohol?

tertiary alcohol

example: classify the alcohol

secondary

example: classify the alcohol

secondary

how does the number of carbons effect solubility?

as the number of carbons increases, solubility decreases

what is the relative boiling points of alcohols, and why?

• relatively high boiling points

• they have hydrogen bonding

  • H covalently bonded to unshared pair on an O,N, or F

example: name the following

isopropyl alcohol

which fxn group has an -OH attached to an aromatic ring (benzene)?

phenol

example: name the following

4-bromophenol

what is the solubility of phenols, and why?

• slightly soluble in water

• the OH makes hydrogen bonds when reacted with water

what do phenols act as in a reaction?

• weak acids

• acids are the H+ donor

  • acid/conj. base…

identify the fxn group

• ether

• has a C-O-C linkage

fxn group with a C-O-C linkage?

ethers

what type of connectivity to ethers have?

dipole-dipole

are ethers or alcohols more soluble in water?

• alcohols

  • they have hydrogen bonds and ethers do not

example: name the following

butyl propyl ether

identify the fxn group

• thiol

• has an SH attached to an alkane

what is the polarity and solubility of thiols?

• nonpolar

  • don’t have H bonds bc no H covalently bonded to O,N,F

• limited solubility in water as a result

which fxn group has an SH attached to alkanes?

thiols

example: name the following

2-butanethiol

what fxn group has CSC linkage?

sulfides

identify the fxn group

• sulfide

• has CSC linkage

what is the solubility and polarity of sulfides/disulfides?

• limited solubility

• nonpolar

  • do not have H bonds

when does an alcohol chain become insoluble?

if it has 5 or more carbons

• the OH can no longer make it soluble as the carbons increase

what fxn group has CSSC linkage?

disulfides

identify the fxn group

disulfide

example: name the following

dimethyl sulfide

example: name the following

dipropyl disulfide

identify the fxn group

• aldehyde

• carbonyl group (C=O) is on the end of a carbon chain

which fxn group has a carbonyl (C=O) group attached on the end of the carbon chain?

aldehydes

which fxn group has a carbonyl (C=O) group attached in the middle of carbon chain?

ketones

identify the fxn group

• ketone

• the carbonyl (C=O) is in the middle of two carbons

example: name the following

3-methylcyclohexanone

what does solubility look like for aldehydes and ketones?

• it varies

• bc of the amount of carbons

  • 5+ carbons = insoluble

  • less than 5 = soluble

what parts of aldehydes and ketones makes them polar (sometimes)?

• carbonyl group has partially negative oxygen atom and a partially positive carbon atom

• makes it polar

what type of forces do aldehydes and ketones have?

• london

• dipole-dipole

how does the boiling point for aldehydes/ketones compare that of alcohols?

• lower boiling point than alcohols

• they don’t have hydrogen bonding

nucleophile def

• electron rich atom/group

• electron pair donor

• negatively charged/neutral

electrophile def

• electron poor atom/group

• electron pair acceptor

• positively charged

what type of reaction is this?

nucleophilic substitution reaction

describe what happens during a nucleophilic substitution reaction

• element attached to the long carbon chain switches places with the element that is being added

• one pair of electrons from the original element moves to the other element

• the other element gains a negative charge

name the products of the following reaction

diethyl sulfide

identify the nucleophile in the following reaction

• the OH

• it is donating electron pair, its electron rich

what happens during oxidation?

• gaining of O bonds

• losing of H bonds

when an alcohol is oxidized, what fxn group is formed?

• a carbonyl group (C=O)

  • either aldehyde or ketone

describe what happens during primary alcohol oxidation

• the OH loses the H

• a double bond forms to the O

• this makes it into an aldehyde/ketone

• when aldehyde/ketone is oxidized, and O is added to one of the H’s

• this makes a carboxylic acid (C=O with and OH group attached to the same carbon)

describe what happens during secondary alcohol oxidation

• the OH loses the H

• H under the carbon leaves

• double bond is formed

what group cannot oxidize?

tertiary alcohols

what is the product of two thiols being oxidized?

• disulfides

• the H’s are removed from the SH’s to make a H2O

carboxylic acid is a acid or base?

• weak acid

• H+ donor

identify the reaction type

• benedicts reagent oxidation

• only affecting an aldehydes, not primary/secondary alcs

• uses copper (Cu2+)

which type of reaction involves using copper as the oxidizing agent (on the arrow in the reaction)?

benedicts reagent

• “benedict took some copper”

which type of reaction only effects aldehydes, and not alcohols?

benedicts reagent

describe what happens during benedicts reagent reaction

• the H that is attaches to the C or the carboxylic acid of an aldehyde turns into an O-

what’s the product of the following reaction?

what is the relative boiling points of caboxylic acids?

• relatively high

• they have H bonds

how do carboxylic acids act in water?

• weak acids

• acids = H+ donors

identify the fxn group

• ester

• C-O-C linkage where one carbon is a carbonyl (C=O)

what functional group has C-O-C linkage and one carbon has a carbonyl (C=O) group?

esters

identify the fxn group

• amine (ammonia)

• has NH3

how are amines classified?

• primary = 1 carbon directly attached to nitrogen

• secondary = 2 carbon directly attached to nitrogen

• tertiary = 3 carbon directly attached to nitrogen

identify the reaction type

• acid hydrolysis

• there is an ester reacting with H+ and heat

• think of it as HOH

what is different for an amine that is quarternary?

the nitrogen has a +1 charge

classify the following amine

• quarternary

• N has +1 charge

whats the ending for naming amines?

-amine

name the following

n-ethyl-n-methyl-ethanamine

what is a benzene ring with an amine on it called?

aniline

identify the fxn group

• aniline

• there is a benzene ring with an amine

which amines can hydrogen bond?

primary and secondary

which type of amines have the highest boiling points?

primary, seconday, and tertiary

what happens when an amine has more than 6 carbons?

• decreased solubility

• basically eliminates the effect of hydrogen bonding

what are amines when in a reaction?

• weak bases

• so they accept H+

describe an amide.

• carboxylic acid group

• instead of -OH, there -NH2