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Give the numbers from the reagent table for the sequence of reactions that will convert ethanol to t-butyl alcohol.
(2 18 15 18 .... 15 18 ...and

1. HNO3. H2S04 2. PCC 3. Na2Cr207. H2904 4. 8r2. FeBra 5. PBr3 6. H2C-О 7. 1. LiAIH4 2. H30+, H2O 8. HBr 9. H2O, H+ 10. CHgCH2CH2CI, AICI3 11. CH3CH2CH-PPh3 12. Zn-Hg. EtOH, HCI 13. Li THF 14. 1. CH3CH2CH2MgCI 2. H20, Ht 15 KMnO4 16. HOCH2CH2OH, H3ot 17. CH3CH2OH, H 20. 1. BH3 2. H2O2. NaOH 18. 1. 2 CHgli 2. H30, H2O 19.1. BuLi 2. H30+,H2O

15 9 15 9 are all incorrect)

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Answer #1

The reagents are: 3, 18

Explanation: Oxidation of primary alcohol with Na2Cr2O7, H2SO4 produces carboxylic acid as product. Reaction of carboxylic acid with organolithium reagent produces tertiary alochol as product.

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