exam 2

alkyl halide

halogen atom that is directly attached to an sp³‑hybridized carbon of an alkyl group

vinylic halide

halogen atom that is directly attached to an sp²‑hybridized carbon of a non‑aromatic alkene

aryl halide

halogen atom that is directly attached to an sp²‑hybridized carbon of a benzene (or other aromatic ring)

ester group

thioester

acid halide

anhydride

amide

nitrile

naming anhydride

acid name + anhydride

eg. acetic anhydride

naming acid chloride

aklanoyl chloride

eg. ethanoyl chloride

naming ester

alkyl + alkanoate

eg. ethyl acetate

cyclic ester

lactone

cyclic amide

lactam

increasing bp factors for carboxylic acids

• more intermolecular forces

• more hydrogen bonding

• largr molecules

amide resonance

nitrogen lone pair pariticipates in resonance with carbonyl

amide IR

1650-1675

ESTER IR

1735-1745

ACID CHLORIDE IR

1800

ANNHYDRIDE IR

two peak around 1760 and 1820

NITRILE IR

2200-2250

CARBOXYLIC ACID IR

C=O 1700

O-H 2400-3200

amide N-H NMR

7.5-8.5 ppm

carbonyl carbon NMR c=o

165-180 ppm

nitrile carbon NMR

115-120ppm

reactivity order

acid chloride> anhydride> thioester > ester> amide

reactivity depends on

good leaving group(weak base) and resonance stabalization

what reaction

acid chloride hydrolysis

what reaction

anyhdride hydrolysis

what reaction

acid catalyzed ester hydrolysis

• reverse of fishcer esterification

• products: carboxylic acid and alcohol

what reaction

ester base hydrolysis

saponificiaton

• becomes carboxylic acid by adding h3o+

what reaction

amide hydrolysis

what reaction

nitrile hydrolysis

• amide intermediate

acetyl chloride

propanoyl chloride

priority for principal groups

acid>nitrile>aldehdye>ketone>thiols>alcohol>hydrate

why is acteonitrile important

useful polar, aprotic solvent

H NMR for amides

7.8-8.5 ppm

eliminated by exchange with D2O

C=O NMR

165-180

C triple bond N NMR

115-120

valerate

malonate