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At this time I'm just trying to setup the simplest of apps where I click a button and that will send the most basic of transactions to my testrpc network. It's easy to do with JS and web3, but how can I do this with Ruby on Rails ?

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There are many ways to connect with ethereum,

recently I used this coinfalcon

1: https://docs.coinfalcon.com/ this for both python and ruby.this provide api for place order with the help of this.

Ethereum Ruby

This help to you connect with ethereum, Here you can do:

1 IPC Client Connection
2 Solidity contract compilation and deployment
3 Transacting and Calling Solidity Functions

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