7 bints eBook O References Be sure to answer all parts. Draw a stepwise mechanism and the product for the following substitution reaction: Hint Guided Soluti H.C- NaOCH3 acetone finish structure draw structure ** OOO I I CHI ۵

complete the following syntheses

5. Draw the products of the following reactions: HBr ether Lindlar catalyst NAOH H2O, heat ...Br H2O H;0 heat CN OH PBrs H3C CH3 ether ČH3 H3C CH, CH3CH2CH2OH water H3C Li CH;CH2 -C=C-CH3 NH3

34) A mixture of cis- and trans- 1,2-dimethylcyclohexan-1-ol is heated in concentrated H3PO4. Which of th following is predicted to be the major alkene product(s)? conc. HзPОд OH ??? (cis- & trans-) (-H20) a) c) d) b)

Complete the following reactions by identifying the majority product(s) or the reaction conditions that are missing. No mechanism is needed

Dehydration of 1,2,2-trimethylcyclohexanol with H2SO4 affords 1-tert-butylcyclopentene as a minor product. (a) Draw a stepwise mechanism that shows how this alkene is formed. (b) Draw other alkenes formed in this dehydration. At least one must contain a ve-membered ring.

Ff.166.

The appropriate product of the following reaction is: H3C- (a) (b) H3C H3C CH3 H3CO CH3 CH3 L S ******** H3CO S 1. Br₂, CH3OH 2. NaSCH 3, DMSO R CH3 SCH3 CH3 S CH3 SCH3 +R, S + R, R (c) (d) H3C. H3C H3CS CH3 ******** H3CS S S R CH3 OCH3 CH3 S CH3 OCH3 +R, S +R, R

6. The product(s) of the following reaction dd blow di CH2-CH2 excess HBr is/are: CH2 CH2 heat Od Al () (A od Ocf D (CHPPCOK (CHPCON G)D CH;CH2OCH,CH3 HO CH;CH,CH,CH,OH and CH;CH,CH2CH,Br II H t mol boumol toubong soinm od o CH2-CHBR HO CH2 CH2 BrCH-CH,CH-Cн,ОН and BrCH,CH,CH-CH,Br CityCHCH COM III IV A) I B) П O II D) IV E) None of these HO CH CH'OH

CH3 o alengoiga6 916w vtalmedoociote 6. Plan syntheses of the following compounds. You may use the given starting material and any compound containing three or fewer carbons. () (a) Br Br Br (d) of (b) ОН ОН (o) Оама (c) (b). (d) Br C Br ОН (e) CI (e) CI CI CI