Ans_Second_Review_Prob_Set

Ans_Second_Review_Prob_Set - P1 OXT/SRB P2 PBY...

Info iconThis preview shows pages 1–6. Sign up to view the full content.

View Full Document Right Arrow Icon
P1: OXT/SRB P2: PBY Printer: Hamilton JWDD052-ANSWER JWDD052-Solomons-v3 April 30, 2007 11:14 ANSWERS TO SECOND REVIEW PROBLEM SET These problems review concepts from Chapters 13–21. 1. O (a) (b) (c) (d) (e) O OH O O OMe MeO < << OH O OH O Cl NH 2 OH O Cl Cl OH Increasing acidity CC H OH < < < < < OH < (CH 3 ) 3 C O OH + (CH 3 ) 3 N O OH O NH 2 < O O NH O OH O OH 2. Increasing basicity O (a) (b) (c) NH 2 NH 2 NH 3 CH 3 < < < < < (d) NH 2 NH 2 NH 2 NH 2 CH 3 < NH 2 O 2 N NH 2 O CH 3 CH 3 N H CH 3 CH 3 490
Background image of page 1

Info iconThis preview has intentionally blurred sections. Sign up to view the full version.

View Full Document Right Arrow Icon
P1: OXT/SRB P2: PBY Printer: Hamilton JWDD052-ANSWER JWDD052-Solomons-v3 April 30, 2007 11:14 ANSWERS TO SECOND REVIEW PROBLEM SET 491 3. (a) (b) (c) (d) OH Br PBr 3 (or HBr) Br [from part (a)] O O NK N O O NH 2 + NH 4 + + H 2 NNH 2 heat O O N N H H [from part (a)] Br CN LiAlH 4 Et 2 O NaCN NH 2 OH (1) KMnO 4 , OH , heat (2) H 3 O + OH O (e) (g) [from part (c)] CN H 3 O + , H 2 O heat OH O (f ) [from part (f)] NH 3 Cl O NH 2 O [from part (d)] SOCl 2 Cl O OH O (h) (i) + CO 3 2 [from part (f)] base Cl O OH O O (1) Br 2 , OH (2) H 3 O + [from part (g)] NH 2 O NH 2
Background image of page 2
P1: OXT/SRB P2: PBY Printer: Hamilton JWDD052-ANSWER JWDD052-Solomons-v3 April 30, 2007 11:14 492 ANSWERS TO SECOND REVIEW PROBLEM SET (j) AlCl 3 HCl Zn (Hg) [from part (f)] Cl O O (k) [from part (f)] Cl O ONa O O 2 (l) (1) OH , H 2 O, heat (2) H 3 O + [from part (a)] Br O OEt OEt O Na + O OEt OEt O O OH OH O O O OH heat CO 2 4. (a) CH 3 OH (1) O (2) H 3 O + PCC CH 2 Cl 2 OH (aldol condensation) CH 3 CH 3 (separate from ortho isomer) Br CH 3 MgBr Br 2 FeBr 3 Mg Et 2 O CH 3 [(E) or (Z)] H O CH 3 CH 3 H O
Background image of page 3

Info iconThis preview has intentionally blurred sections. Sign up to view the full version.

View Full Document Right Arrow Icon
P1: OXT/SRB P2: PBY Printer: Hamilton JWDD052-ANSWER JWDD052-Solomons-v3 April 30, 2007 11:14 ANSWERS TO SECOND REVIEW PROBLEM SET 493 (b) HF base CCl 4 ( hv ) NBS (2) H 2 O 2 , OH (1) BH 3 : THF Br OH (2) (1) NaH O Br NH 2 N H O (c) Cl 2 , FeCl 3 (separate from ortho isomer) O 2 O N H Cl O NH 2 Cl NH 2 Cl OH H 2 O heat Br 2 H 2 O (1) HONO, 0–5 ° C (2) H 3 PO 2 Br Br Cl Br Br
Background image of page 4
P1: OXT/SRB P2: PBY Printer: Hamilton JWDD052-ANSWER JWDD052-Solomons-v3 April 30, 2007 11:14 494 ANSWERS TO SECOND REVIEW PROBLEM SET CH 3 O 2 N LiAlH[OC(CH 3 ) 3 ] 3 diethyl ether 78 ° C (1) H 2 Lindlar’s catalyst (3) H 2 CrO 4 (2) (i) Hg(OAc) 2 , THF-H 2 O (ii) NaBH 4 NBS CCl 4 ( hv ) NaC CH HCN H 3 O + OH SOCl 2 (e) O OH O 2 N O H O O O 2 N O Cl O 2 N O [(E) or (Z)] [(E) or (Z)] O OH CN heat H 2 O OH OH O OH Br CH 3 CH 3 O 2 N (1) KMnO 4 , OH , heat (2) H 3 O +
Background image of page 5

Info iconThis preview has intentionally blurred sections. Sign up to view the full version.

View Full Document Right Arrow Icon
Image of page 6
This is the end of the preview. Sign up to access the rest of the document.

{[ snackBarMessage ]}

Page1 / 14

Ans_Second_Review_Prob_Set - P1 OXT/SRB P2 PBY...

This preview shows document pages 1 - 6. Sign up to view the full document.

View Full Document Right Arrow Icon
Ask a homework question - tutors are online