CHEM 215: Exam 3

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42 Terms

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Conjugated dienes

cis: same side

trans: opposite sides (more stable)

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spirobicycles

2 rings connected by a single atom

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Fused bicycles

2 rings that share 2 atoms

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bridged bicycles

2 atoms that share more than 2 atoms

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Diels alder reactions

  • are faster when 1 SM has an electron withdrawing group and the other has an electron donating group

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Heat

the only necessary reagent for diels alder reactions

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exo

substituent points to smaller bridge

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endo

substituent points to bigger bridge

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limitations to endo/exo

Can not be used for bridges that are the same size

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type of reaction diels alder is

  • addition reaction

  • cycloaddition reactions

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number of bonds formed

3 pi bonds → 1 pi + 2 sigma

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types of dienes

  • isolated: sp3 carbon with no delocalized electrons

  • cumulative: sp hybridized carbon

  • conjugated: delocalization is possiblr

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oxidation of aldehydes in carbohydrates

forms carboxylic acids

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reagents of oxidation

  • AgNO3, NH3, Ag2O, NaOH

  • CuSO4, NaOH,

  • Br2,H2O

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addition reactions of carbonyls reagents

-CH3OH/cat acid

- PhCh2SH/cat acid

-NaCN/H2O

-RONH2/PH6

-NaBH4/CH3OH

-CH3NH2/PH6

-PhNHNH2/PH6

<p>-CH3OH/cat acid</p><p>- PhCh2SH/cat acid</p><p>-NaCN/H2O </p><p>-RONH2/PH6</p><p>-NaBH4/CH3OH</p><p>-CH3NH2/PH6</p><p>-PhNHNH2/PH6</p>
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CH3OH/cat acid

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PhCh2SH/cat acid

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NaCN/H2O

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RONH2/PH6

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NaBH4/CH3OH

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CH3NH2/PH6

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PhNHNH2/PH6

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addition and acylation reactions of hydroxyls reagents

-everything is in excess!

-CH3I/NaH

-(CH3O)2SO2/NaOH

-PhCH2Br/NaH

-PhCOCl/N(CH2CH3)3

-CH3COOCOCH3/pyradine

<p>-everything is in excess!</p><p>-CH3I/NaH </p><p>-(CH3O)2SO2/NaOH </p><p>-PhCH2Br/NaH </p><p>-PhCOCl/N(CH2CH3)3 </p><p>-CH3COOCOCH3/pyradine </p>
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CH3I/NaH

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(CH3O)2SO2/NaOH

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PhCH2Br/NaH

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PhCOCl/N(CH2CH3)3

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CH3COOCOCH3/pyradine

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reducing sugar

must contain an aldehyde or hemiacetal

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N-Terminus protecting groups

use base

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BOC2O

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CBZ

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FMOC

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C-terminus protecting groups

use acids (i.e H2SO4)

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OtBu

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OBn

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OMe

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DCC

- acylating agent used to form peptide bonds

-helps add amino acids with protecting groups onto other amino acids

<p>- acylating agent used to form peptide bonds</p><p>-helps add amino acids with protecting groups onto other amino acids</p>
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isoelectric point

Ph where the molecule carries no electrical charge

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Products of diels alder

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H2O/H2SO4

- can break acetals/ketals into mixed alcohols

-can not work on OCH2Ph unless it is an anomeric alcohol

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CH3OH/H2SO4

-only works on anomeric alcohol