1)Which of the following alkanes will give more than one monochlorination product when treated with chlorine and light?a)2,2-dimethylpropane, b) cyclopropnae, c) ethane, d) 2,3-dimethylbutane

2) Which type of halogenation is most selective? Bromination is most selective, always occurring at the site of the most stable radical.

3) Which of the following absorbs at the highest frequency? a) 1,3,5-hexatriene, b) 1,3,5,7-octatetraene, c) 1,7-diphenyl-1,3,5-heptatiene, d) 1,6-diphenyl-1,3,5-heptatriene

4) Draw 3,5-difluoroanisole.

1 5) Circle each of the following compounds that is aromatic.

4n + 2 = 10 pi electrons4n + 2 = 2 pi electrons

1)6) Which of the following compounds will undergo Fredal-Crafts alkylation?a)a) benzoic acid, b) nitrobenzene, c) aniline, d) toluene

7) Which of the following compounds is most acidic?

8) Which of the following gives a secondary alcohol when treated with methyl grignard?a) butyl formate, b) 3-pentanone, c)pentanal, d) methyl butanoate

9) Draw N-ethyl-N-propylformamide.

10) What does a positive iodoform test tell you is present It indicates the presence of a methyl ketone.

11)12)

13)14)

15)16)

17)18)

19)20)

Molecular ion peak is a single peak at 164, so no halogens or nitrogen.

164/12 = 13 x 12 =156164 156 = 8 hydrogensC13H82(13) + 2 8 = 20/2 = 10C12H20

2(12) + 2 20 = 6/2 = 3

C11H16O

2(11) + 2 16 = 8/2 = 4

C10H12O22(10) + 2 12 = 10/2 = 5

Looking at this you have sp2 and sp3 hydrogens as well at a carbonyl.

You have 5 aromatic protons, so most likely a benzene ring is present, so that takes 4 of your five degrees of unsaturation. And the final degree is taken by the carbonyl.

8 different types of carbon, 4 of those are taken up by a monosubstituted benzene ring. You know this because of the 4 peaks in the 120 to 140 range. And the fact that there are 5 aromati protons.

So what is the substituent . We have 4 carbons and 2 oxygens left, plus 7 hydrogens. You know there is a carbonyl so that is one carbon plus one oxygen. What is the other oxygen?So it could either be an ether, an alcohol, or part of an ester. We know it isnt an alcohol b/c there is no large peak around 3400 in the IR.So ester or ether?

This is not an ether b/c at least one of the remaining 3 carbons would be a singlet somewhere up field and that isnt present. So it must be an ester.

So here are all the possible esters, which one is it?

For the nonaromatic protons we see a triplet a multiplet and a quartet, The multiplet tells you that the three carbons are in a group together.

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