16. Using only reagents discussed in your textbook/worksheets, how would you carry out two (3) of the following syntheses? (a) OH T CH3-CH₂-CH₂ (b) HC3 ECH (c) CH3 CH₂-C-CH3 C H .OH

14 Write the IUPAC name for each unsaturated hydrocarbon. (a) CH,=CH(CH,) CH, 4 CH3 CH3 (b) HO (c) H₂C CH3 CH3 (d) (CH₂)₂CHCH=C(CH3)2 (e) CH₂(CH₂)5C=CH (f) CH₂CH₂C=CC(CH3)3 (g)

4. Provide reagents for the following conversions. Show the structures of any intermediates. a) H 0 b) c) 0 CCH₂ d) -CH=CH2 H 0 (CH3)2CHCH2COCH₂CH₂ HO O CNHCH3 Ph C=CHCH2Ph O Et O (CH3)2CHCH2C CH(CH3)2

This question is based on the five compounds (A-E) given in the picture.  1) Would you expect any of the five compounds to have a pleasant, fruity aroma? Explain.

Draw the structural formula for the product formed when propanal reacts with CH,CH – PCHsla Draw Your Solution What are these two isomers? Select the correct answer from below. H. H. Но- HO- CH,CH, CH,CH, H;C H3C (R) (S) (R) (R) Но H. H C-C HO C-C' CH,CH, CH,CH, H;C H;C (S) (S) (R) (R) НО H H HO- + "H "H H,C CH,CH, H;C CH,CH, (S) (R) (R) (R)

The following ethers can, in principle, be synthesized by two different combinations of haloalkane or halocycloalkane and metal alkoxide. Show one combination that forms ether bond (1) and another that forms ether bond (2). Which combination gives the higher yield of ether?

What is the expected product of this reaction scquence? NaC CCH CHCH Br Na THE hgNH (А) CH,CH,CH,с — сн CH,CH, (D) (B) (с сн, сH,сH, Cн СH, CH CH,CH CH,

2

Looking at the following reactions, give the proper iupac name to the reactants or products that are missing.

12. Each of the following conversions requires more than one step. Show reagents and experimental conditions necessary to bring about each conversion. ó- -5 (а) Br COOH (b) H. OCH3 (c) CH3 OC2H5 toluene ethyl benzoate