Download Chapter 10: Properties, Synthesis, and Uses of Alcohols and more Exams Organic Chemistry in PDF only on Docsity! Chapter 10 1 A. Structure and properties - 1. lone pairs CH3 O H R O H ~106° sp3 H O R sp3 hybrids Chapter 10 2 2. reactivity of lone pairs 3. polar O-H bonds R O Hd- d+ Chapter 10 5 Toxicity of alcohols: ~100 ml for CH3OH density = 0.8 gm/ml therefore 80 gm. ~200 ml for CH3CH2OH needed HO2C NH2 C O NH Ph C O OCH3 H+/H2O heat CH3OH Aspartamine (Nutrasweet®) - the great internet hoax Chapter 10 6 CH3 CH H3C OH H2C CH2 OHOH CH CH3 CH3 OH CH3 2-propanol (iso-propyl alcohol) rubbing alcohol solvent, sterilizing agent 1,2-ethanediol (ethylene glycol) antifreeze in cars Menthol - pepermint flavor in Bianca, Chicalets, etc Chapter 10 7 C. Nomenclature - 1. Get alkane name for longest chain that contains the OH group. 2. Drop the final “e” from alkane and add “ol”. 3. Number so that OH gets the lowest number (OH has priority over, C=C, C C, C-X. 4. If there is a higher priority group in the molecule, then OH is named a “hydroxy” group. (see below) 5. For two OH groups, don’t drop the “e” from the alkane name - add “diol”. † ≡ Priority order (you need to memorize this): 1. Carboxyl acids 2. Carboxylic acid esters 3. Aldehydes 4. Ketones 5. Alcohols 6. Amines 7. Alkenes 8. Alkynes 9. Alkanes 10. Ethers 11. Halides Chapter 10 10 5. addition of acetylides to carbonyl compds. RC CH 1) NaNH2 2) R' C O R" 3) H3O + R C C C OH R" R' E. Grignard reagents 1. Preparation of Grignard reagents R X Mg° ether Mg XR C Mg X d- d+ C Mg X (-) (+) (X=Cl, Br, I) Chapter 10 11 2. uses of Grignard reagents a. reaction with aldehydes and ketones Chapter 10 12 b. with carboxylic acid chlorides and esters i. overall reaction Mg XR2 + R' C Cl O 2) H3O + R C R R' OH Mg XR2 + R' C OR" O 2) H3O + R C R R' OH ii. mechanism Mg XR R' C Cl O + R' C Cl O- R R' C R O + Cl- + Mg XR R' C R O- R R' C R O R C R O R:- + R':- + X X Oo
ether
CH)FHCCHs + (CH3),CuLi —“> CHsCHCCHs + CH,Cu + LiBr
Br
Cl
H Br
a s
c=C
D + (CH3CH)),CuLi
H,C CH,
CHs ether
+ | —_—_
CH; CH,=C— ‘sCuLi
ether
————->
O
CH;
CH,
| CH3
C=CH, | .
+ CH=CcCu + LiCl
CH,
H CH;CH,
~ ”
ace + CH;CH)Cu
HSE CHa + LiBr
I CH;
. ether ;
Cy + (CH3),CuLi ————-> Cy + CH;Cu + Lil
Chapter to
15
Chapter 10 16 F. Reduction reactions 1. general reaction - metal hydrides H:- + R C R' O R C R' O-H R C R' O-H H3O +d+ d- H:- H AlH H H Li -or- H BH H H Na compd. NaBH4 LiAlH4 product R C O H R C OH H H yes yes R C O R' R C OH R' H yes* yes R C O OR' R C OH H H yesno R C O O- R C OH H H no yes no no Chapter 10 17 2. general reaction - hydrogenation R C O R' + H2 Raney Ni R C OH R' H *** We are skipping section 10-12 on thiols*** G. Summary 1. Nomenclature 2. Properties - lone pairs and polar H-O bond 3. Acidity of alcohols and H-bonding 4. Synthesis of alcohols a.review material i. SN2 reactions with -OH ii. hydration of alkenes iii. oxymercuration-demercuration iv. hydroboration - oxidation v. addition of acetylides to C=O
