有机化学：answer of chapter 7

1、Comments on Chapter Seven1. Draw structures corresponding to the following IUPAC names:(a) 2,3-Dichloro-4-methylhexane(b) 4-Bromo-4-ethyl-2-methylhexane(c) 3-Iodo-2,2,4,4-tetramethylpentane(d) cis-1-Bromo-2-ethylcyclopentaneClClBrIC2H5Br2. Predict the products of the following reactions:Comments on

2、Chapter SevenH3C OHHBrEtherH3CBr(a) CH3CH2CH2CH2OHSOCl2CH3CH2CH2CH2Cl(b) NBSCCl4Br(c) OHPBr3EtherBr(d) MgEtherCH3CH2CHBrCH3CH3CH2CHCH3MgBrH2OCH3CH2CH2CH3(e) Comments on Chapter SevenCH3CH2CH2CH2BrEther+ (CH3)2CuLi(g) CH3CH2CH2CH2CH33. Predict the products of the following reactions:LiPentaneCH3CH2CH

3、2CH2Br(f) CH3CH2CH2CH2LiCuI(CH3CH2CH2CH2)2CuLi4. How to complete the following conversion? Comments on Chapter SevenCH2DCH3(1)MgClCH3D2OMgEtherClCH3HClComments on Chapter SevenCH3CH2CNNO2(2)CH2BrNO2NaCNNBSCH3NO2H2SO41) H2SO4, HNO3CH3SO3H2) H2SO4,H2O5. What product would you expect from the reaction

4、of 1-phenyl-2-butene with NBS? Explain. Comments on Chapter SevenNBSCCl4Braba. Benzylic and allylic position, free radical can be delocalized over benzene ring and the double bond. b. Allylic position, free radical can only be delocalized over the double bond.6. Order each of the following sets of c

5、ompounds with respect to SN1 reactivity:Comments on Chapter SevenH3CCClCH3CH3ClH3CCH3CH3CH2CHCH3NH2(1)(2)(3)(a)(1) (2) (3)(1)(2)(3)(b)(CH3)3CCl(CH3)3CBr(CH3)3COH(2) (1) (3)Comments on Chapter Seven(1)(2)CH2BrCHCH3BrCBr3(3)(c)(3) (2) (1)7. Order each of the following sets of compounds with respect to

6、 SN2 reactivity:H3CCClCH3CH3CH3CH2CHCH3Cl(1)(2)(3)(a)CH3CH2CH2Cl(2) (3) (1)(1)(2)(3)(b)CH3CHCHCH3BrCH3CH3CHCH2ClCH3CH3CCH2ClCH3CH3Comments on Chapter Seven(2) (3) (1)(2) (3) (1)CH3SOOOCH2CH2CH3H3CSOOOH对甲基苯磺酸对甲基苯磺酸 TsOHGood leaving group(1)(2)(3)CH3CH2CH2OCH3(c)CH3CH2CH2OTsCH3CH2CH2Br8. How can you e

7、xplain the fact that trans-1-bromo-2-methyl-cyclohexane yields the non-Zaitsav elimination product 3-methyl-cyclohexene on treatment with base?Comments on Chapter SevenCH3HHBrKOHHHCH3CH3non-Zaitsav elimination productZaitsav elimination productE2 elimination reaction：The blue H and Br are anti perip

8、lanar geometry, so the non-Zaitsav product yield.A Summary of Substitution and Elimination ReactionComments on Chapter SevenHalide typeSN1SN2E1E2RCH2X(primary)Does not occurHighly favoredDoes not occurOccurs when strong bulky base are usedR2CHX(secondary)Can occur with benzylic and allylic halidesOccurs in com- petition withE2 reactionCan occur with benzylic and allylic halidesFavored when strong base a