Dehydration of 2-Methylcyclohexanol (continued on the next page): (1) (4 pts) One of the possible minor products in this week's experiment was 4-methylcyclohexene, pictured below. Draw a mechanism for the formation of 4-methylcyclohexene by the the dehydration of 2- methylcyclohexanol. (2) OH cat. H₂PO (1 pt) Modern instruments typically perform an integration of the peak areas for you. Older instruments were not capable of this and chemists would cut out the individual peaks and weigh them to correlate to the peak areas. If you ran the mixture of alkenes from this week's experiment and obtained the following weights for each of the correlating peaks, calculate the % area for each peak. Show your work. Peak A = 0.265 mg Peak B = 1.803 mg Peak C = 0.908 mg

Which reagent/catalyst would be expected to bring about the following conversion? OH CH;CH2CH,CH CH;CH2CH,C-H ÓCH, Ag(NH3)2" / OH CH3OH / H3O* (1) NaBH4 (2) H30* O HNO3 / H2SO4 O K2Cr207/ H2SO4

A student proposes the following two-step synthesis of an ether from an alcohol A and another organic reagent R: A 1. TvCl.py 28 Is the student's proposed synthesis possible and likely to give good yield? If you said the proposed synthesis would work, draw the structures of A and R in the drawing area below. If there's more than one pair of A and R that give equally good results, you can draw any pair. It's OK if R is an lonic species, you can assume any necessary counterion is present. Click and drag to start drawing a structure. 0 4:0 Oyes Ono 2)

4) What is the best way to perform the transformation shown below? CH₂Br ? OH A) 1. NaCN 2. H3O+ 2. CO B) 1.Mg C) concentrated KMnO4 3. H3O+ D) diazomethane E) Both A and B would work

which one is limiting reagent？？

5) Provide the expected mechanism for the following reaction. Please show all intermediates and use arrows to show the movement of electrons (you do not have to show transition states). (1 pt) ii CI NaOH (2 equiv)

how do toluene and n-butanol work wotg the reactants to produce squaraine dye?

3) I have just finished running a chlorination reaction (below) using methanol as my solvent. Cl₂ MeOH A CI CI B OMe CI I only expected to see one product - Product A - but somehow, I seem to have generated 2 different products. How could this have happened? Justify the formation of Product B in 1-2 sentences and draw the relevant mechanistic step(s) (2 pts).

The organic chemistry professor instructed students to synthesize 1-hexanethiol from 1-hexanol. Two students Sophie and Emily, disagreed on what reaction sequence to carry out in the lab. Emily's reaction sequence: 1-hexanol + NaSH --> 1-hexanethiol   Sophie's reaction sequence: 1-hexanol + 1. TsCl, 2. NaSH --> 1-hexanetiol Which is correct, Emily or Sophie?

Part I (Quantitative): a substitution reaction using the tertiary diol below will produce a product that can be isolated and characterized. на хот 2,5-dimethylhexane-2,5-diol conc. HCI The available reaction solutions are: ▪ 18% sodium iodide in acetone ▪ 1% silver nitrate in ethanol 2,5-dichloro-2,5-dimethylhexane m.p. 63-66.5 °C Part II (Qualitative): the substitution of various alkyl halides will provide insight into the effects of substrate structure, leaving group, and reaction temperature on SN2 and SNl reactions, and you will be able to draw conclusions about these reactions based on your observations. The available alkyl halides are listed later in the experimental procedures section. For Part I (Quantitative): a. Draw the overall synthetic reaction, including all structures, relevant physical data, amounts, and safety information. b. Clearly show the calculation (including units throughout) of the theoretical yield of the reaction. Indicate the limiting reagent. For Part II…