2/27/2012

Muscone isa15memberedringketoneusedinperfume.Itwas originallyisolatedfromthemuskdeerbutitisnowpreparedfrom citronellal.

O H

Whatisthestructureofthealkeneintermediateisasynthesisusing citronella?
O O H

muscone

CH3

H citronellal

CH3 H

CH3

H citronellal

CH3

Howcouldmuscone bepreparedfromcitronellal?

?
O O O

muskdeer

lemongrass

CH3

CH3

CH3

Whatcarboncarbonbondformingreactionwouldbebestforthe synthesisoflargerings?
O O H

Whatisthenextlikelyreactioninthissynthesis?
O H

CH3

H citronellal

CH3 H2/Pd-C H O

CH3

H citronellal

CH3

A
Ru H CH3 O

B ? ? C

B
H

CH3

Whatisalikelylaststepinthesynthesisofmuscone fromcitronellal usingolefinmetathesis?

O O H

Howcouldthediene fortheolefinmetathesisreactionbeprepared?
O H

CH3

H citronellal

CH3 H2/Pd-C H O

CH3

H citronellal

CH3

Ru

CH3 O OH

CH3

CH3

2/27/2012

Howcouldcitronellabeconvertedintothealcohol? Howcouldtheorgano lithiumreactantbepreparedfromcompounds containingfourcarbonatomsorless? O

O H

Bond Energies (kJ/mol) C=C = 590 C=O = 803 C=O = 120

H2/Pd-C

H O

CH3

H citronellal

CH3

C=C = 134

Bond Lengths (pm)

fourcarbonatoms orless
Ru H CH3 O OH

C-C = 331

C-O = 326

Why do C=C bonds readily add acids but C=O bonds do not?
H CH3 H CH3

What is the product when a C=O bond adds water? How can the addition of water do double bonds be catalyzed?
O O H

H2/Pd-C

H O

CH3

H citronellal

CH3

Ru

CH3 O OH

CH3

CH3

Do both C=C and C=O readily undergo addition products with acids? A. yes B. no

Isthehydrationofformaldehyde(A)moreor(B)lessthan acetaldehyde?Why?

103.36 (2290)
formaldehyde

Keq

100.03 (1.07)
formaldehyde acetaldehyde

E
G=RTlnKeq

2/27/2012

Whatisanunambiguousnameforthefollowingketone?

10-2.85 (.0014)
acetone A.2isopropyl5methylcyclohexanone B.5isopropyl2methylcyclohexanone

Keq

100.03 (1.07)
acetaldehyde

C.5propyl2methylcyclohexanone D.trans2isopropyl5methylcyclohexanone E.Noneofthese

Isthehydrationof acetaldehyde(A)moreor(B) lessthanacetone?

acetaldehyde
O H H O

E
G=RTlnKeq

Whatisanunambiguousnameforthefollowingketone?

Whatisanunambiguousnameforthefollowingketone?

A.2isopropyl5methylcyclohexanone B.5isopropyl2methylcyclohexanone O O C.5propyl2methylcyclohexanone D.trans2isopropyl5methylcyclohexanone E.(2R,5R)2isopropyl5methylcyclohexanone

menthone
O H

F.Noneofthese
H O

Pennyroyal (Mentha pulegium)

Whatisanunambiguousnameforthefollowingketone?

Whatisanunambiguousnameforthefollowingketone?

A.2isopropyl5methylcyclohexanone B.5isopropyl2methylcyclohexanone O C.5propyl2methylcyclohexanone D.Noneofthese O

A.2isopropyl5methylcyclohexanone B.5isopropyl2methylcyclohexanone C.5propyl2methylcyclohexanone D.trans2isopropyl5methylcyclohexanone E.(2R,5R)2isopropyl5methylcyclohexanone F.Noneofthese

(2S,5R)2isopropyl5methylcyclohexanone
H H

2/27/2012

Howcouldthefollowingtransformationbeaccomplished?

O H

ThedistinctiveFrangipanihasawarm, melodiousscent.Ithasmemoriesof honeysuckleandjasmine,butis neither.Thisuniquefragranceoillingers ontheskin,reminiscentofawarm summereveningwhentheheatofthe dayhaswarmedthescentofthe flowerstoarichcocktailoffloralnotes withahintofhoney.

Howcanthiscompoundbeprepared? Whatisagoodmechanismforthefollowingtransformation?

Whatisagoodmechanismforthefollowingtransformation? Whatisthestructureofthefirstintermediate?